Home Cart Sign in  
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 85822-16-8 Chemical Structure| 85822-16-8

Structure of 85822-16-8

Chemical Structure| 85822-16-8

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 85822-16-8 ]

CAS No. :85822-16-8
Formula : C7H5ClO3S
M.W : 204.63
SMILES Code : O=S(C1=CC=C(C=O)C=C1)(Cl)=O
MDL No. :MFCD01861215
InChI Key :MSWSPWGBDIQKKR-UHFFFAOYSA-N
Pubchem ID :2759210

Safety of [ 85822-16-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:1759
Packing Group:

Application In Synthesis of [ 85822-16-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 85822-16-8 ]

[ 85822-16-8 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 85822-16-8 ]
  • [ 150-76-5 ]
  • [ 106939-94-0 ]
  • 3
  • [ 85822-16-8 ]
  • [ 106-47-8 ]
  • [ 816450-54-1 ]
  • 5
  • [ 85822-16-8 ]
  • [ 95-76-1 ]
  • N-(3,4-dichlorophenyl)-4-formylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
242 mg (75%) With pyridine; In dichloromethane; A. N-(3,4-Dichloro-phenyl)-4-formyl-benzenesulfonamide. Scheme 4. To a stirred solution of 3,4-dichloroaniline (174 mg, 1.07 mmol) and pyridine (0.08 mL, 1.07 mmol) in CH2Cl2 (4.0 mL), was added 200 mg (0.98 mmol) of <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong>. The mixture was stirred at room temperature for 16 h under N2. The solvent was removed under reduced pressure to give a red semi-solid. Purification by chromatography (silica gel, 5% methanol/CH2Cl2) afforded 242 mg (75%) of N-(3,4-dichloro-phenyl)-4-formyl-benzenesulfonamide as a pale tan solid. TLC (silica, 5% methanol/CH2Cl2): Rf=0.4. HPLC: Rt=9.33. MS (ESI-): mass calculated for C13H9Cl2NO3S, 328.97; m/z found, 328.0 [M-H]-. 1H NMR (400 MHz, CD3OD): 10.61 (s, 1H), 8.09 (d, J=8.6 Hz, 2H), 8.04 (d, J=8.5 Hz, 2H), 7.42 (d, J=8.7 Hz, 1H), 7.34 (d, J=2.5 Hz, 1H), 7.06-7.04 (dd, J=8.6, 2.6 Hz, 2H).
  • 6
  • [ 85822-16-8 ]
  • 2-(4-phenylsulfamoyl-phenyl)-1<i>H</i>-benzoimidazole-5-carboxylic acid amide [ No CAS ]
  • 7
  • [ 85822-16-8 ]
  • 2-[4-(4-Chloro-phenylsulfamoyl)-phenyl]-1H-benzoimidazole-5-carboxylic Acid Amide [ No CAS ]
  • 8
  • [ 85822-16-8 ]
  • 2-[4-(3,4-Dichloro-phenylsulfamoyl)-phenyl]-1H-benzoimidazole-5-carboxylic acid amide [ No CAS ]
  • 9
  • [ 85822-16-8 ]
  • [ 100-46-9 ]
  • N-benzyl-4-formyl-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With triethylamine; In dichloromethane; at 20℃; for 17h; To a solution of <strong>[85822-16-8]4-formyl-benzenesulfonyl chloride</strong> (200 mg, 0.978 mmol) and benzylamine (105 mg, 0.978 mmol) in anhydrous CH2Cl2 (3.3 mL) was added triethylamine (198 mg, 1.96 mmol) dropwise. The mixture was stirred at RT for 17 h, and then diluted with saturated aqueous NaHCO3. The aqueous layer was extracted with ethyl acetate (X3), and the combined organic extracts were washed with brine and dried (MgSO4). The solvent was removed under reduced pressure, and the residue was purified by chromatography (silica gel, 20% EtOAc/hexanes) to provide 197 mg (73%) of the title compound as a white solid. HPLC (Method C): Rt=6.01. MS (ESI): mass calculated for C14H13NO3S, 275.1; m/z found, 274.2 [M-H]-. 1H NMR (400 MHz, CDCl3): delta 10.1 (s, 1H), 8.05-8.00 (m, 4H), 7.30-7.28 (m, 3H), 7.21 (dd, J=2.2, 9.6 Hz, 2H), 5.15 (bt, J=6.0 Hz, 1H), 4.23 (d, J=6.1 Hz, 2H). 13C NMR (100 MHz, CDCl3): delta 191.3, 145.7, 139.2, 136.2, 130.6, 129.2, 128.5, 128.3, 128.2, 47.8.
With triethylamine; In dichloromethane; at 0 - 20℃; for 3.5h; To a cold (O0C) solution of 4-formylbenzene-l-sulfonyl chloride (1.04 g, 5.08 mmol) in CH2Cl2 (15 mL) at was added dropwise benzylamine (0.58 mL, 5.34 mmol). Triethylamine (0.78 mL, 5.59 mmol) was then added and the mixture was allowed to stir at 0C for 30 minutes after which time the cooling bath was removed. After stirring the mixture for 3 hours at room temperature, the mixture was diluted with aqueous saturated NaHCO3 solution. The aqueous layer was extracted three times with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude residue (1.23 g) was used without further purification: 1H NMR (300 MHz, CDCl3) delta 10.04 (s, IH), 8.39 (m, 2H), 7.21 (m, 2H), 7.13 (m, 5H), 5.13 (m, IH, NH), 4.14 (d, J= 5.0 Hz, 2H); ESI" MS: m/z (rel intensity) 274 (100, M-H).
  • 10
  • Br(1-)*C27H41N2O4S2Si(1+) [ No CAS ]
  • [ 85822-16-8 ]
  • C34H45N2O7S3Si(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 1h; To a stirred solution of the product of Preparation 15 (1 mmol) and triethylamine (167 muL, 1.2 mmol) in dichloromethane (5 mL) is added <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (225 mg, 1.1 mmol). After stirring for 1 h at room temperature, the solvent is removed under reduced pressure and the resulting crude residue is purified by flash chromatography to give the title intermediate.
  • 11
  • [ 743460-48-2 ]
  • [ 85822-16-8 ]
  • [ 743461-19-0 ]
YieldReaction ConditionsOperation in experiment
62% With triethylamine; In dichloromethane; at 20℃; for 1h; Preparation 27 Biphenyl-2-ylcarbamic Acid 1-{2-[(4-Formylbenzenesulfonyl)methylamino]-ethyl}piperidin-4-yl Ester To a stirred solution of the product of Preparation 8 (350 mg, 1 mmol) and triethylamine (167 muL, 1.2 mmol) in dichloromethane (5 mL) was added <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (225 mg, 1.1 mmol). After 1 h at room temperature, the reaction was complete by MS and the reaction mixture was then washed with saturated aqueous sodium bicarbonate solution (5 mL). The organic layer was then dried (Na2SO4) and solvent removed under reduced pressure to give the title intermediate (323 mg, 62% yield). MS m/z M+H+=522.4.
  • 12
  • 2-[(S)-1-(2-methylaminoethyl)pyrrolidin-3-yl]-2,2-diphenylacetamide [ No CAS ]
  • [ 85822-16-8 ]
  • 2-((S)-1-{2-[(4-formylbenzenesulfonyl)methylamino]ethyl}pyrrolidin-3-yl)-2,2-diphenylacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 1h; To a stirred solution of the product of Preparation 21 (1 mmol) and triethylamine (167 TL, 1.2 mmol) in dichloromethane (5 mL) is added 4-FORMYLBENZENESULFONYL chloride (225 mg, 1.1 mmol). After 1 h at room temperature, the reaction mixture is washed with saturated aqueous sodium bicarbonate solution (5 mL). The organic layer is then dried (NA2S04) and solvent is removed under reduced pressure to give the title intermediate.
  • 13
  • [ 849350-96-5 ]
  • [ 85822-16-8 ]
  • [ 881017-36-3 ]
YieldReaction ConditionsOperation in experiment
80% With dmap; In dichloromethane; at 20℃; for 4h; Step B: N-[2-tert-Butyl-l-(tetrahydro-2H-pyran-4-ylmethyl)-lH-benzimidazol-5- yI]-4-formyl-N-methylbenzenesulfonamide 2-tert-Butyl-N-methyl- 1 -(tetrahydro-2H-pyran-4-ylmethyl)- 1 H-benzimidazol-5- amine (for preparation, see Steps B to F of Example 1) (500 mg, 1.66 mmol) and DMAP (40 mg, 0.332 mmol) were dissolved in 50 mL of DCM. A- Formylbenzenesulfonyl chloride (407 mg, 1.99 mmol) was added and the solution was stirred at rt for 4h. The solution was washed with saturated aqueous NaHCO3 solution, brine and dried over anhydrous MgSO4. The product was purified by silica gel flash chromatography using 65% to 100% EtOAc / hexanes. Yield: 620 mg (80%); 1H NMR (400 MHz, CHLOROFORM-D) delta 1.50 - 1.57 (m, 13 H), 2.25 - 2.35 (m, 1 H), 3.26 (s, 3 H), 3.30 - 3.38 (m, 2 H), 3.99 (t, J=3.03 Hz, 1 H), 4.02 (t, J=2.93 Hz, 1 H), 4.20 (d, J=7.42 Hz, 2 H), 7.19 - 7.22 (m, 1 H), 7.23 (d, J=2.15 Hz, 1 H), 7.28 - 7.32 (m, 1 H), 7.76 (d, J=8.20 Hz, 2 H), 7.96 (d, J=8.59 Hz, 2 H), 10.10 (s, 1 H).
dmap; In dichloromethane; at 20℃; for 2 - 3h;Product distribution / selectivity; Example 52 N-[2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-4- (HYDROXYMETHYL)-N-METHYLBENZENESULFONAMIDE; 2-tert-Butyl-N-methyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-amine (35 mg, 0. 116 mmol) and <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (29 mg, 0. 139 MMOL) were stirred in 3 mL of DCM containing a catalytic amount of DMAP at rt for 2h. The solution was washed with aqueous NAHC03 solution, brine and dried over anhydrous MgSO4. The solvent was evaporated. The residue was dissolved in MeOH (5 mL) and NaCNBH3 (20 mg, 0.298 mmol) was added. The solution was STIRRED overnight at rt. The solvent was evaporated. The residue was dissolved in EtOAc and washed with aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The solvent was evaporated. The crude product was purified by silica gel TLASH CHROMATOGRAPHY using EtOAc as eluent. Yield: 55 mg (78%). H NMR (400 MHz, METHANOL-D4) (TFA salt) : 8 1. 50-1.56 (m, 2 H), 1.57 - 1. 65 (m, 2 H), 1. 68 (s, 9 H), 2.31-2. 41 (m, I H), 3.26 (s, 3 H), 3.35 (td, J=11. 57,2. 64 Hz, 2 H), 3.93 (d, J=3. 32 Hz, 1 H), 3.96 (d, J=3.71 Hz, 1 H), 4.52 (d, J=7.42 Hz, 2 H), 4.68 (s, 2 H), 7.30 (dd, J=8.98, 2.15 Hz, 1 H), 7.50 (s, 4 H), 7.54 (d, J=1. 56 Hz, 1 H), 7.87 (d, J=8.98 Hz, 1 H); MS (ESI) (M+H) + 472. 0; Anal. Calcd for C25H33N304S + 1. 5 TFA + 0. 3 O : C, 51. 89; H, 5.46 ; N, 6.48. Found: C, 51.94 ; H, 5.48 ; N, 6. 31.; Example 54 N-[2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-4- { [(2-hydroxyethyl)amino]methyl}-N-methylbenzenesulfonamide; 2-TERT-BUTYL-N-METHYL-1-(TETRAHYDRO-2H-PYRAN-4-YLMETHYL)-1 H-BENZIMIDAZOL-5-AMINE (58 mg, 0. 192 MMOL) and <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (47 mg, 0.230 mmol) were stirred in 5 mL of DCM containing a catalytic amount OF DMAP at rt for 3h. The solution was washed with aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The solvent was evaporated. The residue was dissolved in MeOH (5 mL) containing a few drops OF ACOH and 3A molecular sieves. Ethanolamine (0.057 mL, 0.960 mmol) was added and the solution was stirred at rt for 30 min. NaCNBH3 (36 mg, 0.576 MMOL . was added and the solution was stirred at rt for 3h. The solvent was evaporated. The residue was dissolved in EtOAc and washed with aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The product was purified by reversed-phase HPLC using 10-60% CH3CN/H2O and LYOPHILIZED affording the title compound as the corresponding TFA salt. Yield: 48 mg (40%). H NMR (400 MHz, METHANOL-D4): 8 1.49-1. 55 (m, 2 H), 1.55-1. 61 (m, 2 H), 1.67 (s, 9 H), 2.32-2. 39 (m, 1 H), 3.15-3. 18 (m, 2 H), 3.27 (s, 3 H), 3.34 (dt, J=11. 47,2. 64 HZ, 2 H), 3. 81 (dd, J=5.96, 4.39 Hz, 2 H), 3.92 (d, J=3.12 Hz, 1 H), 3.95 (d, J=3.71 Hz, 1 H), 4.33 (s, 2 H), 4.51 (d, J=7.62 Hz, 2 H), 7.28 (dd, J=9. 08, 2.05 Hz, 1 H), 7.56 (d, J=1.95 Hz, 1 H), 7.61-7. 68 (m, 4 H), 7.85 (d, J=8. 98 Hz, 1 H) ; MS (ESI) (M+H) + 515. 2; Anal. Calcd for C27H3SN404S + 2.7 TFA + 0.9 H2O : C, 46.40 ; H, 5. 11 ; N, 6. 68. Found: C, 46.41 ; H, 5.05 ; N, 6.75.
With dmap; In dichloromethane; at 20℃; for 2 - 3h;Product distribution / selectivity; Example 32; N-[2-TERT-BUTYL-L-(TETRAHYDRO-2H-PYRAN-4-YLMETHYL)-LH-BENZIMIDAZOL-5-YL]-4- (HYDROXYMETHYL)-N-METHYLBENZENESULFONAMIDE; 2-TERT-BUTYL-N-METHYL-L- (TETRAHYDRO-2H-PYRAN-4-YLMETHYL)-LH-BENZIMIDAZOL-5-AMINE (35 mg, 0.116 mmol) and 4-FORMYLBENZENESULFONYL chloride (29 mg, 0. 139 mmol) were stirred in 3 ML of DCM containing a catalytic amount of DMAP at rt for 2h. The solution was washed with aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The solvent was evaporated. The residue was dissolved in MEOH (5 mL) and NaCNBH3 (20 mg, 0.298 mmol) was added. The solution was stirred overnight at rt. The solvent was evaporated. The residue was dissolved in EtOAc and washed with aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The solvent was evaporated. The crude product was purified by silica gel flash chromatography using EtOAc as eluent. Yield: 55 mg (78%). 1H NMR (400 MHz, METHANOL-D4) (TFA salt): 8 1.50-1. 56 (m, 2 H), 1.57-1. 65 (m, 2 H), 1.68 (s, 9 H), 2.31-2. 41 (m, 1 H), 3.26 (s, 3 H), 3. 35 (td, J=11. 57,2. 64 Hz, 2 H), 3.93 (d, J=3. 32 Hz, 1 H), 3.96 (d, J=3.71 Hz, 1 H), 4.52 (d, J=7.42 Hz, 2 H), 4.68 (s, 2 H), 7.30 (dd, J=8.98, 2.15 Hz, 1 H), 7.50 (s, 4 H), 7.54 (d, J=1.56 Hz, 1 H), 7.87 (d, J=8.98 Hz, 1 H); MS (ESI) (M+H) +472. 0; Anal. Calcd for C2SH33N304S + 1.5 TFA + 0.3 H2O : C, 51.89 ; H, 5.46 ; N, 6.48. Found: C, 51.94 ; H, 5.48 ; N, 6. 31; Example 34; N-[2-tert-Butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-4- {1 (2-HYDROXYETHYL) AMINO] METHYL}-N-METHYLBENZENESULFONAMIDE; 2-tert-Butyl-N-methyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-amine (58 mg, 0.192 mmol) and 4-FORMYLBENZENESULFONYL chloride (47 mg, 0. 230 mmol) were stirred in 5 ML of DCM containing a catalytic amount of DMAP at rt for 3h. The solution was washed with aqueous NAHC03 solution, brine and dried over anhydrous MgS04. The solvent was evaporated. The residue was dissolved in MEOH (5 mL) containing a few drops OF ACOH and 3A molecular sieves. Ethanolamine (0.057 mL, 0.960 mmol) was added and the solution was stirred at rt for 30 MIN. NACNBH3 (36 mg, 0.576 mmol) was added and the solution was stirred at rt for 3h. The solvent was evaporated. The residue was dissolved in EtOAc and washed with aqueous NAHC03 solution, brine and dried over anhydrous MGS04. The product was purified by reversed-phase HPLC using 10-60% CH3CN/H20 and lyophilized affording the title compound as the corresponding TFA salt. Yield: 48 mg (40%). H NMR (400 MHZ, METHANOL-D4) : 8 1.49-1. 55 (M, 2 H), 1.55-1. 61 (m, 2 H), 1.67 (s, 9 H), 2.32-2. 39 (m, 1 H), 3.15-3. 18 (M, 2 H), 3.27 (s, 3 H), 3.34 (dt, J=11. 47,2. 64 Hz, 2 H), 3.81 (dd, J=5.96, 4. 39 HZ, 2 H), 3.92 (d, J=3. 12 Hz, 1 H), 3.95 (d, J=3. 71 Hz, 1 H), 4.33 (s, 2 H), 4.51 (d, J=7. 62 Hz, 2 H), 7.28 (dd, J=9.08, 2.05 Hz, 1 H), 7.56 (d, J=1.95 Hz, 1 H), 7.61-7. 68 (M, 4 H), 7.85 (d, J=8.98 Hz, 1 H); MS (ESI) (M+H) + 515.2 ; Anal. Calcd for C27H3SN404S + 2.7 TFA + 0.9 H20: C, 46.40 ; H, 5. 11 ; N, 6.68. Found: C, 46.41 ; H, 5.05 ; N, 6.75.
With dmap; In dichloromethane; at 20℃; for 3h; 2-tert-Butyl-iV-methyl- 1 -(tetrahydro-2H-pyran-4-ylmethyl)- l/f-benzimidazol-5-amine (58 mg, 0.192 mmol) (for preparation, see the following steps B to E) and a catalytic amount of DMAP were dissolved in 5 mL of DCM. 4-Formylbenzenesulfonyl chloride (47 mg, 0.230 mmol) was added and the solution was stirred at rt for 3h. The solution was washed with saturated aqueous NaHCO3, brine and dried over anhydrous Na2SO4. The solvent was evaporated. The residue was then dissolved in 5 mL of EPO <DP n="23"/>MeOH containing a few drops of glacial AcOH. Ethanolamine (0.057 mL, 0.960 mmol) and powdered 3A molecular sieves (500 mg) were added. The solution was stirred at rt for 30 min. NaCNBH3 (36 mg, 0.576 mmol) was added and the solution was stirred at rt for 3h. The solution was filtered and the solvent evaporated. The residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3, brine and dried over anhydrous Na2SO4. The solvent was evaporated and the product was purified by reversed-phase HPLC using 10-70% CH3CN/H2O and lyophilized affording the title compound as the corresponding TFA salt. Yield: 48 mg (40%). 1H NMR (400 MHz, METHANOL-D4): delta 1.49 - 1.55 (m, 2 H), 1.55 - 1.61 (m, 2 H), 1.67 (s, 9 H), 2.32 - 2.39 (m, 1 H), 3.15 - 3.18 (m, 2 H), 3.27 (s, 3 H), 3.34 (m, 2 H), 3.81 (dd, J=5.96, 4.39 Hz, 2 H), 3.92 (d, J=3.12 Hz, 1 H), 3.95 (d, J=3.71 Hz3 1 H), 4.33 (s, 2 H), 4.51 (d, J-7.62 Hz, 2 H), 7.28 (dd, J=9.08, 2.05 Hz, 1 H)3 7.56 (d, J=I.95 Hz, 1 H), 7.61 - 7.68 (m, 4 H), 7.85 (d, J=8.98 Hz, 1 H); MS (ESI) (M+H)+ 515.0; Anal. Calcd for C27H38N4O4S + 2.7 TFA + 0.9 H2O: C3 46.40; H, 5.11; N, 6.68. Found: C, 46.41; H, 5.05; N3 6.75.;Following the same procedure described in Example 2, Step A, using 2-tert-butyl-iV- methyl-l-(tetrahydro-2H"-pyran-4-ylmethyl)-lH-benzimidazol-5-amine (50 mg, 0.166 mmol), DMAP (catalytic) and <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (44 mg, 0.215 mmol) in 5 mL of DCM. Morpholine (0.045 mL, 0.498 mmol) and NaCNBH3 (31 mg, 0.498 mmol) in 5 mL of MeOH were used for the second step. The solvent was evaporated. The product was purified by reversed-phase HPLC using 10-70% CH3CN/H2O and was lyophilized, affording the title compound as the corresponding TFA salt. Yield: 52 mg (48%). 1H NMR (400 MHz, METHANOL-D4): delta 1.52 - 1.57 (m, 2 H), 1.57 - 1.63 (m, 2 H), 1.68 (s, 9 H), 2.33 - 2.41 (m, 1 H), 3.29 (s, 3 H), 3.29 - 3.32 (m, 4 H), 3.35 (m, 2 H), 3.79 - 3.92 (m, 4 H), 3.93 (d, J=3.58 Hz, 1 H), 3.95 (d, J=2.82 Hz, 1 H), 4.45 (s, 2 H), 4.53 (d, J-7.42 Hz, 2 H), 7.32 (dd, J=8.96, 2.05 Hz, 1 H), 7.60 (d, J=I.79 Hz, 1 H), 7.65 - 7.72 (m, 4 H), 7.88 (d, J=8.96 Hz, 1 H); MS (ESI) (M+H)+ 541.0; Anal. Calcd for C29H40N4O4S + 2.9 TFA: C, 47.97; H, 4.96; N, 6.43. Found: C, 48.08; H, 5.06; N, 6.13.; 2-tert-Butyl-iV-methyl- 1 -(tetrahydro-2/f-pyran-4-ylmethyl)- l/f-benzimidazol-5-amine (45 mg, 0.149 mmol) and a catalytic amount of DMAP were dissolved in 3 mL of DCM. 4-Formylbenzenesulfonyl chloride (37 mg, 0.179 mmol) was added and the solution was stirred at rt for 2h. The solution was washed with saturated aqueous NaHCO3, brine and dried over anhydrous Na2SO4. The solvent was evaporated. The residue was then dissolved in 5 mL of MeOH and NaCNBH3 (20 mg, 0.298 mmol) was added. The solution was stirred overnight at rt. The solvent was evaporated. The residue was dissolved in EtOAc and washed with saturated aqueous NaHCO3, brine and dried over anhydrous Na2SO4. The crude product was purified by silica gel flash chromatography using EtOAc as eluent. Yield: 55 mg (78%). 1H NMR (400 MHz, METHANOL-D4): delta 1.50 - 1.56 (m, 2 H), 1.57 - 1.65 (m, 2 H), 1.68 (s, 9 H), 2.31 - 2.41 (m, 1 H), 3.26 (s, 3 H), 3.35 (m, 2 H), 3.93 (d, J-3.32 Hz, 1 H), 3.96 (d, J=3.71 Hz, 1 H), 4.52 (d, J=7.42 Hz, 2 H), 4.68 (s, 2 H), 7.30 (dd, J=8.98, 2.15 Hz, 1 H), 7.50 (s, 4 H), 7.54 (d, J=I.56 Hz, 1 H), 7.87 (d, J=8.98 Hz5 1 H); MS (ESI) (M+H)+ 472.0.; 2-tert-Butyl-N-methyl-l-(tetrahydro-2H-pyran-4-ylmethyl)-lH-benzimidazol-5-amine (250 mg, 0.829 mmol) and DMAP (100 mg, 0.829 mmol) were dissolved in 10 mL of DCM. 4-Formylbenzenesulfonyl chloride (205 mg, 0.995 mmol) was added and the EPO <DP n="33"/>solution was stirred at rt for 2h. The solution was washed with aqueous NaHCO3 solution, brine and dried over anhydrous MgSO4. The crude product was purified by silica gel flash chromatography using EtOAc as eluent. Yield: 288 mg (74%). 1H NMR (400 MHz, CHLOROFORM-D) delta 1.51 - 1.56 (m, 13 H), 2.25 - 2.34 (m, 1 H), 3.26 (s, 3 H), 3.30 - 3.38 (m, 2 H), 3.99 (t, J=2.93 Hz, 1 H), 4.02 (t, J=2.93 Hz, 1 H), 4.20 (d, J=7.42 Hz, 2 H), 7.19 - 7.21 (m, 1 H), 7.23 (d, J=2.15 Hz, 1 H), 7.28 - 7.31 (m, 1 H), 7.76 (d, J=8.20 Hz, 2 H), 7.96 (d, J=8.59 Hz, 2 H), 10.10 (s, 1 H).

  • 14
  • [ 110-91-8 ]
  • [ 85822-16-8 ]
  • [ 77547-10-5 ]
YieldReaction ConditionsOperation in experiment
92% at 0 - 20℃; Morpholine (8.94 g, 102.62 mM; 2.1 eq.) was slowly dropped into a cooled (0 C.) solution of the 4-formylbenzene sulfonyl chloride (10.0 g, 48.87 mM; 1.0 eq.) and the mixture was slowly warmed to ambient temperature. TLC indicated complete disappearance of the starting sulfonyl chloride. The mixture was then poured on to ice-cold water, the solid was filtered, washed with water and vacuum dried to obtain the title sulfonamide as an off-white solid (11.5 g, 92%). The purity read 98% by LC/MS.
  • 15
  • [ 85822-16-8 ]
  • [ 3240-35-5 ]
YieldReaction ConditionsOperation in experiment
With ammonia; In tetrahydrofuran; at 20℃; for 3h; A suspension of 4-formylbenzenesulfonic acid sodium salt (1.0 g, 4.78 mM) in excess of thionylchloride (15 ml) was heated to reflux for 30 minutes. The mixture was then concentrated to dryness, dissolved in anhydrous THF (20 ml). The mixture was cooled (ice-bath) to which was added excess of ammonia (5 ml, 1.0M solution in THF) and the suspension was stirred for 3 hrs at ambient temperature. The reaction was quenched with ice-cold water where up on the amide precipitated out. It was filtered, washed with water and vacuum dried overnight. Efforts were not made to purify the amide and it was used as such in the subsequent reaction. The crude amide was dissolved in methanol (20 ml) and subjected to condensation with N-tert-butylhydroxylamine hydrochloride (0.72 g, 5.74 mM) at refluxing temperature for 6 hrs. Concentration of the mixture followed by silicagel column chromatography afforded the title compound as a white solid. MS: m/z 257 (MH+). 1H NMR delta 1.51(s, 9H); 7.39(brs, 2H); 7.83(d, J=8.8 Hz, 2H); 7.99(s, 1H); 8.49 (d, J=8.8 Hz, 2H).
With ammonia; In 1,4-dioxane; dichloromethane; at 20℃; for 3h; A solution of ammonia (0.5 M in 1,4-dioxane, 5 mL) was added to <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (0.5 g), followed by DCM (10 mL). The reaction mixture was stirred vigorously for 3 h at RT, then concentrated under reduced pressure. The crude residue was purified by flash chromatography to afford 4-formyl-benzenesulfonamide. MS=183.9 [M-H]-.
  • 16
  • tert-butyl 2-[({(2R,3S)-2-hydroxy-3-[((2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanoyl)amino]-4-phenylbutyl}amino)methyl]pyrrolidine-1-carboxylate [ No CAS ]
  • [ 85822-16-8 ]
  • tert-butyl 2-[(({4-[(hydroxyimino)methyl]phenyl}sulfonyl)-{(2R,3S)-2-hydroxy-3-[((2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanoyl)amino]-4-phenylbutyl}amino)methyl]pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
A solution of the product of Example 274D (85 mg) in dichloromethane (0.6 mL) was treated with triethylamine (17 muL, 2 equivalents) and <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (12 mg, 1 equivalent), stirred at 25 C. for 2 hours and concentrated. A solution of the residue in methanol (1 mL) was treated with hydroxylamine hydrochloride, stirred at 25 C. for 16 hours and concentrated. The residue was purified by HPLC reverse phase chromatography using water (0.1% trifluoroacetic acid):acetonitrile (95:5) to acetonitrile (100%) to give 16 mg (20% over 3 steps) of the title compound.
  • 17
  • [ 13736-22-6 ]
  • [ 85822-16-8 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; for 0.5h;Heating / reflux; A suspension of 4-formylbenzenesulfonic acid sodium salt (1.0 g, 4.78 mM) in excess of thionylchloride (15 ml) was heated to reflux for 30 minutes. The mixture was then concentrated to dryness, dissolved in anhydrous THF (20 ml). The mixture was cooled (ice-bath) to which was added excess of ammonia (5 ml, 1.0M solution in THF) and the suspension was stirred for 3 hrs at ambient temperature. The reaction was quenched with ice-cold water where up on the amide precipitated out. It was filtered, washed with water and vacuum dried overnight. Efforts were not made to purify the amide and it was used as such in the subsequent reaction. The crude amide was dissolved in methanol (20 ml) and subjected to condensation with N-tert-butylhydroxylamine hydrochloride (0.72 g, 5.74 mM) at refluxing temperature for 6 hrs. Concentration of the mixture followed by silicagel column chromatography afforded the title compound as a white solid. MS: m/z 257 (MH+). 1H NMR delta 1.51(s, 9H); 7.39(brs, 2H); 7.83(d, J=8.8 Hz, 2H); 7.99(s, 1H); 8.49 (d, J=8.8 Hz, 2H).
  • 18
  • [ 849351-88-8 ]
  • [ 85822-16-8 ]
  • N-[2-(1,1-difluoroethyl)-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-4-formyl-N-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With dmap; N-ethyl-N,N-diisopropylamine; at 60℃; 4-Formylbenzenesulfonyl chloride (238 mg, 1.16 mmol) was added to a solution of 2- (1 , 1 -difluoroethyl)-iV-methyl- 1 -(tetrahydro-2H-pyran-4-ylmethyl)- 17i"-benzimidazol- 5-amine (300 mg, 0.96 mmol), DIPEA (0.23 mL, 1.35 mmol) and DMAP (118 mg, 0.96 mmol). The reaction mixture was heated to 60C overnight and the solvent was concentrated. The product was recovered in EtOAc and washed with saturated NaHCO3 solution, water and brine. The organic solution was dried over anhydrous Na2SO4 and the solvent was concentrated. The product was purified on silica gel by MPLC using EtOAc 10 to 90% in heptane to provide the title compound as white solid. Yield: 454 mg (98%); MS (ESI) (M+H)+ 478.2.
  • 19
  • [ 849434-60-2 ]
  • [ 85822-16-8 ]
  • [ 881377-22-6 ]
YieldReaction ConditionsOperation in experiment
With dmap; In 1,1-dichloroethane; at 20℃; <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (591 mg, 2.89 mmol) was added to a solution of 2- tert-butyl- 1 -[(4,4-difluorocyclohexyl)methyl]-N-methyl- lH-benzimidazol-5-amine (808 mg, 2.40 mmol) and DMAP (30 mg, 0.25 mmol) in DCE (15 mL) at room temperature. The reaction mixture was stirred overnight. The solvent was removed; the crude product recovered in EtOAc (250 mL), washed with saturated NaHCO3 solution (3x50 mL), brine and dried over anhydrous Na2SO4. The title compound was obtained as a white solid and used for the next step without further purification.
  • 20
  • [ 461-82-5 ]
  • [ 85822-16-8 ]
  • [ 920536-28-3 ]
YieldReaction ConditionsOperation in experiment
47% With pyridine; In 1,1-dichloroethane; at 20℃; for 5h; Example 68: 4-(5-Oxo-4,5,6,7,8,9-hexahydro-2H-1,2,7,9-tetraazabenz[f]inden-4-yl)-N-(4-trifluoromethoxy-phenyl)-benzenesulfonamide; compound with trifluoro-acetic acid Preparation of the aldehyde: to a mixture of 610 mg of 4-chlorosulfonylbenzaldehyde (3 mmoles) and 460 mg of 4-trifluoromethoxyaniline (3 mmoles) in 2 ml of dichloroethane is added 2 ml of pyridine (25 mmoles). The reaction mixture is stirred at room temperature for 5 hours and then poured into 100ml of 10% HCl solution. The mixture is extracted with twice 30 ml of DCM. The combined organic phases are washed with 30 ml of water; 30 ml of saturated solution of sodium bicarbonate and brine, the solution is dried over MgS04 and evaporated. The crude is purified on silica gel using DCM/AcOEt 90/10 as eluent. 0.48g of 4-formyl-N-(4-trifluoromethoxy-phenyl)-benzenesulfonamide is isolated as a white solid (yield=47%). ([M+H]+): 346. Ret. Time: 5.53 min (gradient 5 to 85 % acetonitrile in 7 min).
  • 21
  • [ 96-50-4 ]
  • [ 85822-16-8 ]
  • [ 933683-83-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In dichloromethane; for 1.5h; To a solution of <strong>[85822-16-8]4-formyl-benzenesulfonyl chloride</strong> (0.49 mmol) in dichloromethane and pyridine (5 mL, 4:1) was added thiazol-2-ylamine (0.49 mmol), and the resulting mixture EPO <DP n="41"/>was stirred for 1.5 h before it was concentrated in vacuo. The residue was suspended in concentrated ammonium hydroxide (5 mL) and l-phenyl-propane-l,2-dione (0.49 mmol) was added. The mixture was stirred at 80 0C for 4 h before it was cooled to room temperature and concentrated in vacuo. The mixture was extracted with AcOEt and the organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by reverse phase HPLC to give 0.1 mmol of 4-(5-methyl-4-phenyl-lH-imidazol-2-yl)-N- thiazol-2-yl-benzenesulfonamide.[0155] 1H NMR (300 MHz, DMSO-d6): delta 8.19 (d, J = 8.4 Hz, 2H), 8.05 (d, J = 8.4 Hz, 2H), 7.71 (d, J = 8.4 Hz, 2H), 7.06-7.44 (m, 3H), 7.22 (d, J = 4.6 Hz, IH), 6.96 (d, J = 4.6 Hz, IH), 2.51 (s, 3H); MS m/z: 397 (M + 1).
  • 22
  • [ 91-21-4 ]
  • [ 85822-16-8 ]
  • [ 1057490-85-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 1h; A solution of 4-formylbenzene sulfonyl chloride (1) (0.40 g, 1.95 mmol) in dichloromethane (5 mL) was treated with 1,2,3,4-tetrahydroisoquinoline (0.28 mL, 2.15 mmol) and triethylamine (0.33 mL, 2.34 mmol). The resultant mixture was stirred at room temperature for 1 h. A saturated aqueous solution of sodium bicarbonate (10 mL) was added. The product was extracted three times with 10 mL of dichloromethane. The combined organic layers were dried over potassium carbonate, filtered and concentrated. The crude material (0.67 g) was used in the next reaction without purification: Crude 1H NMR (400 MHz, CDCl3) delta 10.08 (s, IH), 8.03-7.97 (m, 4H), 7.20-7.00 (m, 4H), 4.31 (s, 2H), 3.42 (t, J= 6.0 Hz, 2H), 2.90 (t, J= 6.0 Hz, 2H); ESI+ MS: m/z (rel intensity) 302.0 (100, [M+H]+).
  • 23
  • [ 496-12-8 ]
  • [ 85822-16-8 ]
  • [ 780777-94-8 ]
YieldReaction ConditionsOperation in experiment
96% With triethylamine; In dichloromethane; at 20℃; for 1h; A solution of 4-formylbenzene sulfonyl chloride (1) (0.50 g, 2.44 mmol) in dichloromethane (5 mL) was treated with isoindoline (0.32 g, 2.68 mmol) and triethylamine (0.41 mL, 2.93 mmol). The resultant mixture was stirred at room temperature for 1 h. A saturated aqueous solution of sodium bicarbonate (10 mL) was added. The product was extracted three times with 10 mL of dichloromethane. The combined organic layers were dried over potassium carbonate, filtered and concentrated in vacuo. The crude material (0.67 g, 96% yield) was used in the next reaction without purification: Crude 1H NMR (400 MHz, CDCl3) delta 10.06 (s, IH), 8.05-8.00 (m, 4H), 7.25-7.20 (m, 2H), 7.20-7.14 (m, 2H), 4.66 (s, 4H); ESI+ MS: m/z (rel intensity) 288.0 (100, [M+H]+).
  • 24
  • [ 937072-66-7 ]
  • [ 85822-16-8 ]
  • [ 937074-18-5 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0℃; for 16h; Example 19 2,2'-[[(4-formylphenyl)sulfonyl]imino}bis(methylene)]bis(N,N-dimethyl-1H-imidazole-1-sulfonamide) To a dichloromethane(5 mL) solution of the compound (500 mg) obtained in Example 3 and triethylamine (0.27 mL), <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (340 mg) was added at 0C. The reaction solution was stirred at 0C for 16 hours. To the reaction solution, water (30 mL) was added, followed by extraction of the aqueous layer twice with dichloromethane (50 mL). The combined organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. After removing the anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was washed with ethyl acetate and then purified to obtain the title compound (606 mg) having the following physical properties. TLC: Rf 0.67(ethyl acetate); NMR(DMSO-d6):delta 2.83 (s, 12H), 5.01 (s, 4H), 6.86 (d, J=1.8Hz, 2H), 7.48 (d, J= 1.8Hz, 2H), 7.90 (d, J=8.1 Hz, 2H), 8.00 (d, J=8.1 Hz, 2H), 10.06 (s, 1 H).
  • 25
  • [ 109-01-3 ]
  • [ 85822-16-8 ]
  • [ 195155-27-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In dichloromethane; water; for 1h; To a solution of <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (1.0 g) in DCM (10 mL) was added NaHCO3 (sat'd aq, 10 mL) followed by 1-methyl-piperazine (0.6 mL). The reaction mixture was vigorously stirred for 1 h, the organic layer separated, and the aqueous layer extracted with DCM (2*20 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give 4-(4-methyl-piperazine-1-sulfonyl)-benzaldehyde (1.28 g) without further purification.
  • 26
  • [ 85822-16-8 ]
  • [ 100243-39-8 ]
  • 4-(3-hydroxypyrrolidine-1-sulfonyl)-benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In methanol; at 20℃; for 1h; Step A: To <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (1.0 g) in MeOH (10 mL) was added NaHCO3 (0.425 g, s), followed by S-(-)-3-hydroxypyrrolidine (0.533 g), and the mixture stirred at RT for 1 h. The product was filtered through celite, concentrated to provide an oil, and chromatographed on silica (3% MeOH/DCM) to provide 4-(3-hydroxypyrrolidine-1-sulfonyl)-benzaldehyde (1.14 g).
  • 27
  • [ 5382-16-1 ]
  • [ 85822-16-8 ]
  • [ 1080675-49-5 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In dichloromethane; water; at 20℃; for 2h; Step A: To <strong>[85822-16-8]4-formyl-benzenesulfonyl chloride</strong> (1.0 g) in DCM (10 mL) was added 4-hydroxypiperidine (0.984 g), followed by NaHCO3 (10 mL, aq sat'd) and the mixture stirred for 2 h at RT. The aqueous layer was washed with DCM (2*25 mL), and the combined organic portions washed with brine, dried over Na2SO4, filtered, and the solvent removed under reduced pressure to provide 4-(4-hydroxypiperidine-1-sulfonyl)benzaldehyde. The product was purified on anhydrous silica (10% MeOH/DCM). M+H 269.9
  • 28
  • [ 1070871-24-7 ]
  • [ 85822-16-8 ]
  • [ 1070870-97-1 ]
YieldReaction ConditionsOperation in experiment
75% With triethylamine; In dichloromethane; for 1h; To a solution of methyl {4-(6-fluoro-3'-methyl-2-biphenylyl)-4-hydroxy-4-[(3i?)-3-piperidinyl]butyl}carbamate (75 mg, 0.181 mmol) and triethylamine (0.038 mL, 0.272 mmol) in CH2Cl2 (3.6 mL) was added <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (41 mg, 0.199 mmol). After one hour the reaction was concentrated. The residue was purified via silica gel chromatography (5-50% ethyl acetate/hexanes) to afford methyl (4-(6-fiuoro-3'-methyl-2-biphenylyl)-4- [(3R)- 1 -[(4-formylphenyl)sulfonyl]-3- piperidinyl}-4-hydroxybutyl)carbamate (78.7 mg, 75%) as a white foam. MS (m/z) 582.8 (M+H+).
  • 29
  • [ 85822-16-8 ]
  • [ 2854-16-2 ]
  • [ 1080675-44-0 ]
YieldReaction ConditionsOperation in experiment
With sodium hydrogencarbonate; In methanol; at 20℃; for 1h; Step A: To a solution of 4-formyl-benzene sulfonyl chloride (1.0 g) in MeOH was added NaHCO3 (0.425 g), followed by 1-amino-2-methylpropan-2-ol (0.566 g). The reaction mixture was stirred for 1 h at RT, then filtered through Celite and the solvent removed under reduced pressure to provide 4-formyl-N-(2-hydroxy-2-methylpropyl)-benzene sulfonamide.
  • 30
  • [ 771-61-9 ]
  • [ 85822-16-8 ]
  • [ 1186230-59-0 ]
  • 31
  • [ 85822-16-8 ]
  • [ 160232-08-6 ]
  • [ 605653-52-9 ]
  • 32
  • tert-butyl 2-[({(2R,3S)-2-hydroxy-3-[((2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanoyl)amino]-4-phenylbutyl}amino)methyl]pyrrolidine-1-carboxylate [ No CAS ]
  • [ 85822-16-8 ]
  • C40H54N6O8S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 25℃; for 2h; Example 274Etert-butyl 2-[(({4-[(hydroxyimino)methyl]phenyl}sulfonyl){(2R,3S)-2-hydroxy-3-[((2S)-3-methyl-2-{3-[(2-methyl-1,3-thiazol-4-yl)methyl]-2-oxoimidazolidin-1-yl}butanoyl)amino]-4-phenylbutyl}amino)methyl]pyrrolidine-1-carboxylateA solution of the product of Example 274D (85 mg) in dichloromethane (0.6 mL) was treated with triethylamine (17 muL, 2 equivalents) and <strong>[85822-16-8]4-formylbenzenesulfonyl chloride</strong> (12 mg, 1 equivalent), stirred at 25 C. for 2 hours and concentrated. A solution of the residue in methanol (1 mL) was treated with hydroxylamine hydrochloride, stirred at 25 C. for 16 hours and concentrated. The residue was purified by HPLC reverse phase chromatography using water (0.1% trifluoroacetic acid):acetonitrile (95:5) to acetonitrile (100%) to give 16 mg (20% over 3 steps) of the title compound.
  • 33
  • [ 41838-46-4 ]
  • [ 85822-16-8 ]
  • [ 1336912-64-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20 - 25℃; for 0.5h; Intermediate 14-Formyl-N-( 1 -methylpiperidin-4-yl)benzenesulfonamide1 step a.4-Formylbenzene-l-sulfonyl chloride (0.5 g, 2.44 mmol) was stirred with l-methyl-4- aminopiperidine (CAS RN 41838-46-4) (0.28 g, 2.47 mmol) and triethylamine (0.5 mL, 3.70 mmol) in DCM (10 mL) at rt for 30 min. When the sulfonyl chloride had been used up by tic the reaction mixture was concentrated to give an orange oil (1.1 g) and used without further purification in the next step.
  • 34
  • [ 41838-46-4 ]
  • [ 85822-16-8 ]
  • [ 1336912-20-9 ]
  • 35
  • [ 85822-16-8 ]
  • [ 1228560-66-4 ]
 

Historical Records

Technical Information

• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories