Home Cart 0 Sign in  

[ CAS No. 81900-93-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 81900-93-8
Chemical Structure| 81900-93-8
Structure of 81900-93-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 81900-93-8 ]

Related Doc. of [ 81900-93-8 ]

Alternatived Products of [ 81900-93-8 ]

Product Details of [ 81900-93-8 ]

CAS No. :81900-93-8 MDL No. :MFCD12913768
Formula : C7H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VGLGTAGWVRMFQF-UHFFFAOYSA-N
M.W : 150.13 Pubchem ID :19982202
Synonyms :

Calculated chemistry of [ 81900-93-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.24
TPSA : 72.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.97
Log Po/w (XLOGP3) : 0.46
Log Po/w (WLOGP) : 0.71
Log Po/w (MLOGP) : 0.25
Log Po/w (SILICOS-IT) : 1.32
Consensus Log Po/w : 0.74

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.67
Solubility : 3.24 mg/ml ; 0.0216 mol/l
Class : Very soluble
Log S (Ali) : -1.54
Solubility : 4.32 mg/ml ; 0.0288 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.44
Solubility : 0.54 mg/ml ; 0.0036 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.61

Safety of [ 81900-93-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 81900-93-8 ]

* 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 [ 81900-93-8 ]

[ 81900-93-8 ] Synthesis Path-Downstream   1~28

  • 1
  • [ 186581-53-3 ]
  • [ 81900-93-8 ]
  • [ 108129-33-5 ]
  • 2
  • [ 28955-71-7 ]
  • [ 81900-93-8 ]
YieldReaction ConditionsOperation in experiment
55.5% With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; methanol; under 3102.97 Torr; Preparation of 4-aminobenzo[d]oxazol-2(3H)-one 1b (scheme 2) To compound 4b (1 g, 5.72 mmol) dissolved in a mixture of 4/1 MeOH/THF (50 ml) C/Pd 10% (250 mg) was added and the reaction was hydrogenated at 60 psi overnight. (TLC AcOEt) The reaction was filtrated through a pad of Celite and the filtrate was evaporated under vacuum. The crude solid was crystallized from ether giving 476mg of a white solid. Yield = 55.5%. 1HNMR (DMSO, 200 MHz) delta 5.07 (2H, bs), 6.47 (2H, m), 6.79 (1H, t, J = 8 Hz), 10.93 (1H, bs)
With hydrogen;palladium 10% on activated carbon; In tetrahydrofuran; methanol; under 3102.97 Torr; To compound 4b (1 g, 5.72 mmol) dissolved in a mixture of 4/1 MeOH/THF (50 ml) C/Pd 10% (250 mg) was added and the reaction was hydrogenated at 60 psi overnight. (TLC AcOEt) The reaction was filtrated through a pad of Celite and the filtrate was evaporated under vacuum. The crude solid was crystallized from ether giving 476mg of a white solid. Yield = 55.5%. 'HNMR (DMSO, 200 MHz) delta 5.07 (2H, bs), 6.47 (2H, m), 6.79 (1H, t, J = 8 Hz), 10.93 (1H, bs)
1854.96 kg With platinum on activated charcoal; hydrogen; In 1,2-dichloro-ethane; at 55 - 65℃; under 4500.45 - 6000.6 Torr;Large scale; Mixing the 4-nitro-benzoxazol (IV)-dichloroethane solution obtained in step 3) with 11.5 kg of platinum carbon, venting with nitrogen, stirring, and introducing at 55-65 C. 0.6-0.8MPa hydrogen, stirred to the end of the reaction; the catalyst was recovered by filtration, and the layer was allowed to stand to obtain a solution of 4-amino-2-benzoxazolone (5)-dichloroethane; dichloroethane was distilled to obtain 1854.96 Kg purity 99.1% 4-amino-2-benzoxazolone (V), yield 84.8% (based on 2,6-dinitrochlorobenzene).
  • 3
  • [ 81900-93-8 ]
  • [ 108-24-7 ]
  • [ 99985-17-8 ]
  • 4
  • [ 81900-93-8 ]
  • [ 108-24-7 ]
  • [ 103858-70-4 ]
  • [ 99985-17-8 ]
  • 6
  • [ 81900-93-8 ]
  • [ 32857-62-8 ]
  • [ 1338064-95-1 ]
YieldReaction ConditionsOperation in experiment
48% With diethyl cyanophosphonate; In tetrahydrofuran; at 0 - 80℃; 4-trifluoromethylphenylacetic acid (453 mg, 2.2 mmol) was dissolved in 20 ml of THF and at 0C DEPC (0.43 ml, 1.3equiv) and amine lb (400 mg, 2.66 mmol) were added to the solution. The mixture was warmed at 80C overnight, then evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column using AcOEt as eluant gave 360 mg of a white solid. Yield = 48% 'HNMR (DMSO, 200 MHz) delta 3.80 (2H, s), 7.10 (3H, m), 7.58 (2H, d, J = 8.4 Hz), 7.70 (2H, d, J = 8.2 Hz), 10.06 (1H, bs), 1 1.14 (1H, bs); [M+1] 336.9 (deHnFsNaOs requires 336.3).
48% With diethyl dicarbonate; In tetrahydrofuran; at 0 - 80℃; Example 56: 2-(4-(trifluoromethyl)phenyl)-N-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)acetamide (scheme 10) Preparation of 2-(4-(trifluoromethyl)phenyl)-N-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)acetamide 4-trifluoromethylphenylacetic acid (453 mg, 2.2 mmol) was dissolved in 20 ml of THF and at 0C DEPC (0.43 ml, 1.3equiv) and amine 1b (400 mg, 2.66 mmol) were added to the solution. The mixture was warmed at 80C overnight, then evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column using AcOEt as eluant gave 360 mg of a white solid. Yield = 48% 1HNMR (DMSO, 200 MHz) delta 3.80 (2H, s), 7.10 (3H, m), 7.58 (2H, d, J = 8.4 Hz), 7.70 (2H, d, J = 8.2 Hz), 10.06 (1H, bs), 11.14(1H, bs); [M+1] 336.9 (C16H11F3N2O3 requires 336.3).
  • 7
  • [ 6665-98-1 ]
  • [ 81900-93-8 ]
  • 8
  • [ 603-85-0 ]
  • [ 81900-93-8 ]
  • 9
  • [ 81900-93-8 ]
  • [ 30280-44-5 ]
  • [ 1338064-71-3 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Commercially available p-chlorobenzylamine (1.6 g, 1 1.4 mmol) was dissolved in 60ml of AcOEt and at 0C triphosgene (3.38 g, lequiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 30 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lb (1.7 g, 1 1.4 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 7 / petroleum ether 3). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1 X 50 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 500mg of a white solid. Yield = 14% 'HNMR (DMSO, 200 MHz) delta 4.57 (2H, d, J = 5.8 Hz), 6.53 (2H, m), 7.04 (1H, m), 7.41 (4H, s), 9.88 (1H, t), 1 1.53 (1H, s), 1 1.80 (1H, bs); [M+1] 318.5 (C15H12ClN3O3 requires 317.73).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Example 33: 1-(4-chlorobenzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(4-chlorobenzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available p-chlorobenzylamine (1.6 g, 11.4 mmol) was dissolved in 60ml of AcOEt and at 0C triphosgene (3.38 g, 1equiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 30 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1b (1.7 g, 11.4 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 7 / petroleum ether 3). The solvent was evaporated and the crude was dissolved in AcOEt (80 ml) and washed with water (1 X 50 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 500mg of a white solid. Yield = 14% 1HNMR (DMSO, 200 MHz) delta 4.57 (2H, d, J = 5.8 Hz), 6.53 (2H, m), 7.04 (1H, m), 7.41 (4H, s), 9.88 (1H, t), 11.53 (1H, s), 11.80 (1H, bs); [M+1] 318.5 (C15H12ClN3O3 requires 317.73).
  • 10
  • [ 81900-93-8 ]
  • [ 102422-55-9 ]
  • [ 1338064-62-2 ]
YieldReaction ConditionsOperation in experiment
24% In N,N-dimethyl-formamide; at 80℃; for 8.0h; Preparation of 1-(4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available 4-trifluoromethylbenzylamine (0.5 ml, 3.5 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1 g, 3.5 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1b (350 mg, 2.33 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 200 mg of a white solid. Yield = 24% 1HNMR (DMSO, 400 MHz) delta 4.41 (2H, d, J = 6 Hz), 6.98 (3H, m), 7.05 (1H, m), 7.55 (2H, d), 7.70 (2H, d, J = 8 Hz), 8.49 (1H, bs), 11.00 (1H, bs); [M+1] 352.1 (C16H12F3N3O3 requires 351.28).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Commercially available 4-trifluoromethylbenzylamine (0.5 ml, 3.5 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1 g, 3.5 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound lb (350 mg, 2.33 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 9.5 / MeOH 0.5). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 200 mg of a white solid. Yield = 24% 'HNMR (DMSO, 400 MHz) delta 4.41 (2H, d, J = 6 Hz), 6.98 (3H, m), 7.05 (1H, m), 7.55 (2H, d), 7.70 (2H, d, J = 8 Hz), 8.49 (1H, bs), 1 1.00 (1H, bs); [M+1] 352.1 (C16H12F3N3O3 requires 351.28).
  • 11
  • [ 81900-93-8 ]
  • [ 1338065-53-4 ]
  • [ 1338064-65-5 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Commercially available 4-fluoro-2-trifluoromethylbenzylamine (0.5 ml, 3.7 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.12 g, 3.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5ml) of compound lb (360 mg, 2.4 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 4 / petroleum ether 6). The solvent was evaporated and the crude was dissolved in AcOEt (30ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 90 mg of a white solid. Yield = 10% 'HNMR (DMSO, 200 MHz) delta 4.36 (2H, d, J = 5.6 Hz), 6.71 (1H, t, J = 6 Hz), 6.98 (2H, m), 7.56 (4H, m), 8.55 (1H, bs), 1 1.09 (1H, bs); [M+1] 370.2 (C16HnF4N3O3 requires 369.27).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Example 27: 1-(4-fluoro-2-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(4-fluoro-2-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available 4-fluoro-2-trifluoromethylbenzylamine (0.5 ml, 3.7 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.12 g, 3.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5ml) of compound 1b (360 mg, 2.4 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 4 / petroleum ether 6). The solvent was evaporated and the crude was dissolved in AcOEt (30ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 90 mg of a white solid. Yield = 10% 1HNMR (DMSO, 200 MHz) delta 4.36 (2H, d, J = 5.6 Hz), 6.71 (1H, t, J = 6 Hz), 6.98 (2H, m), 7.56 (4H, m), 8.55(1H, bs), 11.09 (1H, bs); [M+1] 370.2 (C16H11F4N3O3 requires 369.27).
  • 12
  • [ 81900-93-8 ]
  • [ 1338065-54-5 ]
  • [ 1338064-66-6 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Commercially available 4-chloro-2-trifluoromethylbenzylamine (1 g, 4.77 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (1.41 g, 4.77 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound lb (475 mg, 3.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 4 / petroleum ether 6). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 120 mg of a white solid. Yield = 9.7% rHNM (DMSO,200 MHz) delta 4.45 (2H, d, J = 5.6 Hz), 6.99 (4H, m), 7.65 (1H, d), 7.73 (1H, d), 7.85 (1H, bs), 8.62 (1H, bs), 1 1.04 (1H, bs); [M+1] 386.6 (C16HnClF3N3O3 requires 385.73).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Example 28: 1-(4-chloro-2-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea scheme 1) Preparation of 1-(4-chloro-2-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available 4-chloro-2-trifluoromethylbenzylamine (1 g, 4.77 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (1.41 g, 4.77 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1b (475 mg, 3.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 4 / petroleum ether 6). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 120 mg of a white solid. Yield = 9.7% 1HNMR (DMSO, 200 MHz) delta 4.45 (2H, d, J = 5.6 Hz), 6.99 (4H, m), 7.65 (1H, d), 7.73 (1H, d), 7.85 (1H, bs), 8.62 (1H, bs), 11.04 (1H, bs); [M+1] 386.6 (C16H11ClF3N3O3 requires 385.73).
  • 13
  • [ 81900-93-8 ]
  • [ 1338065-33-0 ]
  • [ 1338064-63-3 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Commercially available 2-fluoro-4-trifluoromethylbenzylamine (0.5 ml, 3.7 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (1.12 g, 3.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added drop wise to a solution in DMF (5 ml) of compound lb (360 mg, 2.4 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 100 mg of a white solid. Yield = 1 1 % 'HNMR (DMSO, 400 MHz) delta 4.43 (2H, d, J = 6 Hz), 6.99 (3H, m), 7.05 (1H, m), 7.62 (3H, m), 8.53 (1H, bs), 10.98 (1H, bs); [M+1] 370.1 (C 16H1 1F4N3O3 requires 369.27).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Example 25: 1-(2-fluoro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(2-fluoro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available 2-fluoro-4-trifluoromethylbenzylamine (0.5 ml, 3.7 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (1.12 g, 3.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added drop wise to a solution in DMF (5 ml) of compound 1b (360 mg, 2.4 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 100 mg of a white solid. Yield = 11% 1HNMR (DMSO, 400 MHz) delta 4.43 (2H, d, J = 6 Hz), 6.99 (3H, m), 7.05 (1H, m), 7.62 (3H, m), 8.53 (1H, bs), 10.98 (1H, bs); [M+1] 370.1 (C16H11F4N3O3 requires 369.27).
  • 14
  • [ 81900-93-8 ]
  • [ 1338065-35-2 ]
  • [ 1338064-64-4 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Commercially available 2-chloro-4-trifluoromethylbenzylamine (572 mg, 2.7 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (809 mg, 2.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound lb (270 mg, 1.8 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 70 mg of a white solid. Yield = 10% 'HNMR (DMSO, 400 MHz) delta 4.45 (2H, d, J = 6 Hz), 6.97 (2H, d, J = 4.4 Hz), 7.07 (2H, m), 7.63 (1H, d, J = 8 Hz), 7.74 (2H, d), 7.86 (1H, s), 8.61 (1H, bs), 10.90 (1H, bs); [M+1] 386.6 (C16H11CIF3N3O3 requires 385.7).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Example 26: 1-(2-chloro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(2-chloro-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Commercially available 2-chloro-4-trifluoromethylbenzylamine (572 mg, 2.7 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (809 mg, 2.7 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (5 ml) of compound 1b (270 mg, 1.8 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 70 mg of a white solid. Yield = 10% 1HNMR (DMSO, 400 MHz) delta 4.45 (2H, d, J = 6 Hz), 6.97 (2H, d, J = 4.4 Hz), 7.07 (2H, m), 7.63 (1H, d, J = 8 Hz), 7.74 (2H, d), 7.86 (1H, s), 8.61 (1H, bs), 10.90 (1H, bs); [M+1] 386.6 (C16H11ClF3N3O3 requires 385.7).
  • 15
  • [ 81900-93-8 ]
  • [ 1338065-37-4 ]
  • [ 1338064-67-7 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Amine 2a (1.2 g, 5.5 mmol) (Scheme 7) was dissolved in 40ml of AcOEt and at 0C triphosgene (1.63 g, 5.5 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lb (820 mg, 5.5 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 7 / petroleum ether 3). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 3 0ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 300 mg of a white solid. Yield = 14% 'HNMR (DMSO, 200 MHz) delta 2.51 (6H, s), 4.71 (2H, d, J = 5.6 Hz), 6.55 (2H, d, J = 8.2 Hz), 7.05 (IH, t, J = 7.6 Hz), 7.40 (IH, m), 7.51 (IH, d), 10.06 (IH, bt), 1 1.53 (IH, bs), 1 1.80 (IH, bs); [M+1] 395.1 (C18H17F3N4O3 requires 394.35).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Example 29: 1-(2-(dimethylamino)-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea scheme 1) Preparation of 1-(2-(dimethylamino)-4-(trifluoromethyl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Amine 2a (1.2 g, 5.5 mmol) was dissolved in 40ml of AcOEt and at 0C triphosgene (1.63 g, 5.5 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1b (820 mg, 5.5 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt 7 / petroleum ether 3). The solvent was evaporated and the crude was dissolved in AcOEt (50 ml) and washed with water (1 X 3 0ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 300 mg of a white solid. Yield = 14% 1HNMR (DMSO, 200 MHz) delta 2.51 (6H, s), 4.71 (2H, d, J = 5.6 Hz), 6.55 (2H, d, J = 8.2 Hz), 7.05 (1H, t, J = 7.6 Hz), 7.40 (1H, m), 7.51 (1H, d), 10.06 (1H, bt), 11.53 (1H, bs), 11.80 (1H, bs); [M+1] 395.1 (C18H17F3N4O3 requires 394.35).
  • 16
  • [ 81900-93-8 ]
  • [ 1338065-38-5 ]
  • [ 1338064-68-8 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Amine 2b (289 mg, 1.2 mmol) (Scheme 7) was dissolved in 20ml of AcOEt and at 0C triphosgene (356 mg, 1.2 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lb (180 mg, 1.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave lOOmg of a white solid. Yield = 20% 'HNMR (DMSO, 200 MHz) delta 1.94 (4H, m), 3.23 (4H, m), 4.67 (2H, d, J = 5.6 Hz), 6.55 (2H, dd, J = 8.8 Hz, J' = 1.2 Hz), 7.05 (1H, t, J = 8.2 Hz), 7.17 (2H, d, J = 7.2 Hz), 7.46 (1H, d), 9.98 (1H, t), 1 1.53 (1H, bs), 1 1.80 (1H, bs); [M+1] 421.2 (C2oH19F3N4O3 requires 420.39).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Example 30: 1-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(4-(trifluoromethyl)-2-(pyrrolidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Amine 2b (289 mg, 1.2 mmol) was dissolved in 20ml of AcOEt and at 0C triphosgene (356 mg, 1.2 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1b (180 mg, 1.2 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 100mg of a white solid. Yield = 20% 1HNMR (DMSO, 200 MHz) delta 1.94 (4H, m), 3.23 (4H, m), 4.67 (2H, d, J = 5.6 Hz), 6.55 (2H, dd, J = 8.8 Hz, J' = 1.2 Hz), 7.05 (1H, t, J = 8.2 Hz), 7.17 (2H, d, J = 7.2 Hz), 7.46 (1H, d), 9.98 (1H, t), 11.53 (1H, bs), 11.80 (1H, bs); [M+1] 421.2 (C20H19F3N4O3 requires 420.39).
  • 17
  • [ 81900-93-8 ]
  • [ 1338065-39-6 ]
  • [ 1338064-69-9 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Amine 2c (350 mg, 1.33 mmol) (Scheme 7) was dissolved in 20 ml of AcOEt and at 0C triphosgene (395 mg, 1.33 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lb (100 mg, 0.66 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 40 mg of a white solid. Yield = 14% 'HNMR (DMSO, 400 MHz) delta 1.55 (2H, m), 1.68 (4H, m), 2.85 (4H, m), 4.43 (2H, d, J = 5.6 Hz), 6.88 (1H, t), 6.98 (2H, m), 7.05 (1H, m), 7.31 (1H, s), 7.42 (1H, d), 7.52 (1H, d, J = 8 Hz), 8.52 (1H, s), 1 1.00 (1H, bs); [M+1] 435.3 (C2iH21F3N4O3 requires 434.41).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Preparation of 1-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Amine 2c (350 mg, 1.33 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (395 mg, 1.33 mmol) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and dissolved in 5ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1b (100 mg, 0.66 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 40 mg of a white solid. Yield = 14% 1HNMR (DMSO, 400 MHz) delta 1.55 (2H, m), 1.68 (4H, m), 2.85 (4H, m), 4.43 (2H, d, J = 5.6 Hz), 6.88 (1H, t), 6.98 (2H, m), 7.05 (1H, m), 7.31 (1H, s), 7.42 (1H, d), 7.52 (1H, d, J = 8 Hz), 8.52 (1H, s), 11.00 (1H, bs); [M+1] 435.3 (C21H21F3N4O3 requires 434.41).
  • 18
  • [ 81900-93-8 ]
  • [ 1338065-40-9 ]
  • [ 1338064-70-2 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Amine 2d (362 mg, 3.8 mmol) (Scheme 7) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.12 g, l equiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound lb (384 mg, 2.56 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 200 mg of a pale rose solid. Yield = 18% 'HNMR (DMSO, 400 MHz) delta 2.91 (4H, m), 3.76 (4H, m), 4.46 (2H, d, J = 5.6 Hz), 6.97 (3H, m), 7.05 (1H, m), 7.36 (1H, s), 7.46 (1H, d), 7.54 (1H, d), 8.53 (1H, s), 1 1.00 (1H, bs); [M+1] 437.1 (C2oH19F3N4O4 requires 436.4).
In N,N-dimethyl-formamide; at 80℃; for 8.0h; Example 32: 1-(4-(trifluoromethyl)-2-morpholinobenzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea (scheme 1) Preparation of 1-(4-(trifluoromethyl)-2-morpholinobenzyl)-3-(2,3-dihydro-2-oxobenzo[d]oxazol-4-yl)urea Amine 2d (362 mg, 3.8 mmol) was dissolved in 20 ml of AcOEt and at 0C triphosgene (1.12 g, 1equiv.) was added to the solution. The mixture was warmed at 80C for 4 hours then evaporated and the residue was dissolved in 5 ml of DMF. The solution of the isocyanate was added dropwise to a solution in DMF (10 ml) of compound 1b (384 mg, 2.56 mmol) and the mixture was warmed at 80C for 8 hours. (TLC AcOEt). The solvent was evaporated and the crude was dissolved in AcOEt (30 ml) and washed with water (1 X 20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude residue by chromatographic column gave 200 mg of a pale rose solid. Yield = 18% 1HNMR (DMSO, 400 MHz) delta 2.91 (4H, m), 3.76 (4H, m), 4.46 (2H, d, J = 5.6 Hz), 6.97 (3H, m), 7.05 (1H, m), 7.36 (1H, s), 7.46 (1H, d), 7.54 (1H, d), 8.53 (1H, s), 11.00 (1H, bs); [M+1] 437.1 (C20H19F3N4O4 requires 436.4).).
  • 19
  • [ 603-87-2 ]
  • [ 81900-93-8 ]
  • 20
  • [ 573-56-8 ]
  • [ 81900-93-8 ]
  • 21
  • [ 81900-93-8 ]
  • [ 95-55-6 ]
  • 22
  • [ 81900-93-8 ]
  • [ 19932-87-7 ]
  • 23
  • [ 81900-93-8 ]
  • C14H8N2O4 [ No CAS ]
  • 24
  • [ 81900-93-8 ]
  • [ 2373-98-0 ]
  • 25
  • [ 81900-93-8 ]
  • 3,3'-dihydroxy-4,4'-diaminobiphenyl dihydrochloride [ No CAS ]
  • 26
  • [ 81900-93-8 ]
  • [ 99-57-0 ]
  • [ 121-88-0 ]
  • 27
  • [ 81900-93-8 ]
  • [ 59-49-4 ]
YieldReaction ConditionsOperation in experiment
92.7% With sulfuric acid; copper(II) sulfate; sodium nitrite; In ethyl acetate; isopropyl alcohol;Heating; Large scale; 1854.96 kg of 99.1% pure <strong>[81900-93-8]4-amino-2-benzoxazolone</strong> (V) 763.2 kg of isopropanol, 9274.8 kg of ethyl acetate, 10500 kg of sulfuric acid, 869.8 kg of sodium nitrite, 12.1 kg of copper(II) sulfate were mixed and stirred. The temperature was raised until the end of the reaction; the layer was allowed to stand, and ethyl acetate was distilled off to obtain 1544.6 kg of 2-benzoxazolone (VI) having a purity of 99.3% in a yield of 92.7%.
  • 28
  • [ 606-21-3 ]
  • [ 81900-93-8 ]
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 81900-93-8 ]

Amides

Chemical Structure| 81282-60-2

[ 81282-60-2 ]

7-Aminobenzo[d]oxazol-2(3H)-one

Similarity: 0.90

Chemical Structure| 186663-74-1

[ 186663-74-1 ]

tert-Butyl (2-hydroxyphenyl)carbamate

Similarity: 0.81

Chemical Structure| 13451-79-1

[ 13451-79-1 ]

5-Fluorobenzo[d]oxazol-2(3H)-one

Similarity: 0.81

Chemical Structure| 871367-14-5

[ 871367-14-5 ]

7-Bromobenzo[d]oxazol-2(3H)-one

Similarity: 0.79

Chemical Structure| 184177-81-9

[ 184177-81-9 ]

Phenyl (4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamate

Similarity: 0.79

Amines

Chemical Structure| 81282-60-2

[ 81282-60-2 ]

7-Aminobenzo[d]oxazol-2(3H)-one

Similarity: 0.90

Chemical Structure| 186663-74-1

[ 186663-74-1 ]

tert-Butyl (2-hydroxyphenyl)carbamate

Similarity: 0.81

Chemical Structure| 184177-81-9

[ 184177-81-9 ]

Phenyl (4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)carbamate

Similarity: 0.79

Chemical Structure| 1283176-56-6

[ 1283176-56-6 ]

tert-Butyl (2-methoxy-6-nitrophenyl)carbamate

Similarity: 0.79

Chemical Structure| 159184-15-3

[ 159184-15-3 ]

tert-Butyl 2-(4-aminophenoxy)ethylcarbamate

Similarity: 0.76

Related Parent Nucleus of
[ 81900-93-8 ]

Benzoxazoles

Chemical Structure| 81282-60-2

[ 81282-60-2 ]

7-Aminobenzo[d]oxazol-2(3H)-one

Similarity: 0.90

Chemical Structure| 13451-79-1

[ 13451-79-1 ]

5-Fluorobenzo[d]oxazol-2(3H)-one

Similarity: 0.81

Chemical Structure| 871367-14-5

[ 871367-14-5 ]

7-Bromobenzo[d]oxazol-2(3H)-one

Similarity: 0.79

Chemical Structure| 70735-79-4

[ 70735-79-4 ]

4-Acetylbenzo[d]oxazol-2(3H)-one

Similarity: 0.78

Chemical Structure| 162045-54-7

[ 162045-54-7 ]

3-(Piperidin-4-yl)benzo[d]oxazol-2(3H)-one hydrochloride

Similarity: 0.78