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Chemical Structure| 6396-76-5 Chemical Structure| 6396-76-5
Chemical Structure| 6396-76-5

1-(2,6-Dimethylphenyl)thiourea

CAS No.: 6396-76-5

4.5 *For Research Use Only !

Cat. No.: A501943 Purity: 98%

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Product Details of [ 6396-76-5 ]

CAS No. :6396-76-5
Formula : C9H12N2S
M.W : 180.27
SMILES Code : S=C(N)NC1=C(C)C=CC=C1C
MDL No. :MFCD00041165
InChI Key :ASNKJUONFPQYPC-UHFFFAOYSA-N
Pubchem ID :853911

Safety of [ 6396-76-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301
Precautionary Statements:P264-P270-P301+P310+P330-P405-P501
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis [ 6396-76-5 ]

* 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 [ 6396-76-5 ]

[ 6396-76-5 ] Synthesis Path-Downstream   1~27

  • 2
  • [ 6396-76-5 ]
  • (2,6-dimethyl-phenyl)-[4-(2,6-dimethyl-phenyl)-5-imino-4,5-dihydro-[1,2,4]thiadiazol-3-yl]-amine [ No CAS ]
  • 3
  • [ 6396-76-5 ]
  • [ 87-34-3 ]
  • 4
  • [ 6544-02-1 ]
  • [ 87-62-7 ]
  • [ 6396-76-5 ]
  • 5
  • [ 1147550-11-5 ]
  • [ 87-62-7 ]
  • [ 6396-76-5 ]
  • 6
  • [ 19241-16-8 ]
  • [ 6396-76-5 ]
  • 7
  • [ 75-77-4 ]
  • [ 6396-76-5 ]
  • [ 69859-10-5 ]
  • 8
  • [ 623-46-1 ]
  • [ 6396-76-5 ]
  • [ 54708-12-2 ]
  • 9
  • [ 6396-76-5 ]
  • 3-(2,6-dimethyl-anilino)-4-(2,6-dimethyl-phenyl)-4<i>H</i>-[1,2,4]thiadiazol-5-ylideneamine [ No CAS ]
  • 11
  • [ 6396-76-5 ]
  • [ 74-88-4 ]
  • [ 27806-86-6 ]
  • 12
  • [ 6396-76-5 ]
  • [ 109-77-3 ]
  • [ 159615-60-8 ]
  • 13
  • [ 540-72-7 ]
  • [ 87-62-7 ]
  • [ 6396-76-5 ]
  • 15
  • [ 70-23-5 ]
  • [ 6396-76-5 ]
  • [ 736970-97-1 ]
YieldReaction ConditionsOperation in experiment
In ethanol; at 60℃; To a round-bottomed flask were added 1-(2,6-dimethylphenyl)-2-thiourea (3.0 g, 16.6 mmol, Transworld Chemicals), ethyl bromopyruvate (2.1 mL, 16.6 mmol, Aldrich) and EtOH (40 mL). The reaction mixture was stirred at 60 C. overnight. Solvent was removed in vacuo. Purification by silica gel chromatography (gradient: 0-50% EtOAc in hexane, followed by 0-10% MeOH in CH2Cl2) provided the title compound as a white solid. MS (ESI, pos. ion) m/z: 277 (M+1).
  • 16
  • [ 25343-24-2 ]
  • [ 6396-76-5 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide; at 80℃; for 0.25h; [0335] (2,6-DIMETHYLPHENYL THIOUREA, 20. Solid N-((2,6- dimethylphenyl)carbamothioyl)benzamide (0.50 g, 1.8 mmol) was added in one portion to a 5 mL soln of 5% NaOH heated to 80C. After 15 min of vigorous stirring the mixture is poured into ice-cold 2N HC1. The pH was then adjusted to apprx. 8.5 with Na2C03 and the resulting white solid was collected by filtration, washed with H20, and dried to give 0.24 g (75%) of (2,6- dimethylphenyl)thiourea. 1H-NMR (CDC13; 300 MHz): δ 7.51 (bs, 1H), 7.24-7.19 (m, 1H), 7.16-7.14 (m, 2H), 6.04 (bs, 1H), 5.32 (bs, 1H), 2.31 (s, 6H) ppm.
With sodium hydroxide; at 80℃; Compound 27 Compound 28 Compound 27 (23.46g, 82.49 mmol) was suspended in 200 ml of NaOH (4N) and the mixture was stirred at 80C After the completion of reaction, the temperature was cooled down to room temperature. The Compound 28 was obtained by filtration and washing with 500 ml of H20.
  • 18
  • [ 6396-76-5 ]
  • {2-[(2,6-dimethylphenyl)amino](1,3-thiazol-4-yl)}-N-[4-(trifluoromethyl)-phenyl]carboxamide [ No CAS ]
  • 20
  • [ 6396-76-5 ]
  • C60H62N9O8S3(1+)*Cl(1-) [ No CAS ]
  • 21
  • [ 6396-76-5 ]
  • C29H31N9O7S3 [ No CAS ]
  • 22
  • [ 6396-76-5 ]
  • [ 65070-10-2 ]
  • 23
  • (2,6-Dimethyl-phenylamino)-acetic acid tert-butyl ester [ No CAS ]
  • [ 6396-76-5 ]
  • 24
  • [ 6396-76-5 ]
  • <i>N</i>,<i>N</i>'-bis-(2,6-dimethyl-phenyl)-[1,2,4]thiadiazole-3,5-diamine [ No CAS ]
  • 25
  • [ 6396-76-5 ]
  • [3-(2,6-dimethyl-anilino)-4-(2,6-dimethyl-phenyl)-4<i>H</i>-[1,2,4]thiadiazol-5-ylidene]-phenyl-thiourea [ No CAS ]
  • 26
  • [ 6396-76-5 ]
  • [ 5349-17-7 ]
  • [ 1187669-29-9 ]
YieldReaction ConditionsOperation in experiment
91% Example 1-82 7V-(2,6-Dimethylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (137). [0347] 7V-(2,6-dimethylphenyl)-4-(4-pyridinyl)-l,3-thiazol-2-amine (137). A mixture of bromoketone hydrobromide 1 (0.30 g, 1.1 mmol) and iV-(2,6- difluorophenyl)thiourea (136) (0.20 g, 1.1 mmol) in EtOH (15 mL) was stirred at reflux temperature for 1 h. The mixture was cooled to 20 0C, diluted with water (50 mL), the pH adjusted to ca. 8 with aqueous NH3 and the mixture stirred at 0 0C for 1 h. The precipitate was filtered, washed with water (5 mL) and dried. The crude solid was purified by column chromatography, eluting with EtOAc, to give amine 137 (0.28 g, 91%) as a white powder: mp (EtO Ac/pet, ether) 208-210 0C; 1U NMR δ 9.34 (s, 1 H, NH), 8.55 (dd, J= 4.6, 1.6 Hz, 2 H, H-2', H-6'), 7.72 (dd, J = <n="153"/>4.6, 1.6 Hz, 2 H, H-3', H-5'), 7.46 (s, 1 H, H-5), 7.12-7.19 (m, 3 H, H-3", H-4", H-5"), 2.23 (s, 6 H, 2 x CH3); 13C NMR δ 168.5, 149.9 (2), 147.9, 141.4, 137.7, 135.7 (2), 128.4 (2), 127.0, 119.8 (2), 106.1, 17.8 (2); MS m/z 282.6 (MH+, 100%). Anal, calcd for Ci6Hi5N3S: C, 68.30; H, 5.37; N, 14.93. Found: C, 68.52; H, 5.47; N, 15.14%.
  • 27
  • [ 6396-76-5 ]
  • [ 96-32-2 ]
  • [ 1392735-23-7 ]
YieldReaction ConditionsOperation in experiment
83% With sodium acetate; In ethanol; for 1h;Reflux; Example 11: Preparation of (Z)-2-(2,6-dimethylphenylimino)-3-((£)-4-(l-(4- (trifluoromethoxy)phenyl)-lH-l,2,4-triazol-3-yl)benzylideneamino)thiazolidin-4-one (Compound 81C) (Synthesis Method I) To a solution of l-<strong>[6396-76-5](2,6-dimethylphenyl)thiourea</strong> (1.0 g, 5.55 mmol) in EtOH (10 mL) was added methyl 2-bromoacetate (1.0 g, 6.5 mmol) and sodium acetate (1.0 g, 12.2 mmol). The solution was stirred and heated to reflux for 1 h, then it was cooled and the liquid was decanted from a small amount of solid material and the liquid was then diluted with water (10 mL). The precipitate was isolated by filtration to give (1.1 g, 83%) of (Z)-3-amino-2-(2,6- dimethylphenylimino)thiazolidin-4-one: mp 149-152 C; ]H NMR (400 MHz, CDC13) δ 7.06 (d, / = 7.2 Hz, 2H), 6.98 (m, 1H), 4.75 (s, 2H), 3.80 (s, 2H), 2.12 (s, 6H); ESIMS m/z 236 (M+H).
83% With sodium acetate; In ethanol; for 1h;Reflux; To a solution of <strong>[6396-76-5]1-<strong>[6396-76-5](2,6-dimethylphenyl)thiourea</strong></strong> (1.0 g, 5.55 mmol) in EtOH (10 mL) was added methyl 2-bromoacetate (1.0 g, 6.5 mmol) and sodium acetate (1.0 g, 12.2 mmol). The solution was stirred and heated to reflux for 1 h, then it was cooled and the liquid was decanted from a small amount of solid material and the liquid was then diluted with water (10 mL). The precipitate was isolated by filtration to give (1.1 g, 83%) of (Z)-3-amino-2-(2,6-dimethylphenylimino)thiazolidin-4-one: mp 149-152 C.; 1H NMR (400 MHz, CDCl3) δ 7.06 (d, J=7.2 Hz, 2H), 6.98 (m, 1H), 4.75 (s, 2H), 3.80 (s, 2H), 2.12 (s, 6H); ESIMS m/z 236 (M+H).
83% With sodium acetate; In ethanol; for 1h;Reflux; To a solution of <strong>[6396-76-5]1-<strong>[6396-76-5](2,6-dimethylphenyl)thiourea</strong></strong> (1.0 g, 5.55 mmol) in EtOH (10 mL) was added methyl 2-bromoacetate (1.0 g, 6.5 mmol) and sodium acetate (1.0 g, 12.2 mmol). The solution was stirred and heated to reflux for 1 h, then it was cooled and the liquid was decanted from a small amount of solid material and the liquid was then diluted with water (10 mL). The precipitate was isolated by filtration to give (1.1 g, 83%) of (Z)-3-amino-2-(2,6-dimethylphenylimino)thiazolidin-4-one: mp 149-152 C.; 1H NMR (400 MHz, CDCl3) δ 7.06 (d, J=7.2 Hz, 2H), 6.98 (m, 1H), 4.75 (s, 2H), 3.80 (s, 2H), 2.12 (s, 6H); ESIMS m/z 236 (M+H).
83% With sodium acetate; In ethanol; for 1h;Reflux; Example 11 Preparation of (Z)-2-(2,6-dimethylphenylimino)-3-((E)-4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)benzylideneamino)thiazolidin-4-one (Compound 81C) (Synthesis Method I) To a solution of <strong>[6396-76-5]1-<strong>[6396-76-5](2,6-dimethylphenyl)thiourea</strong></strong> (1.0 g, 5.55 mmol) in EtOH (10 mL) was added methyl 2-bromoacetate (1.0 g, 6.5 mmol) and sodium acetate (1.0 g, 12.2 mmol). The solution was stirred and heated to reflux for 1 h, then it was cooled and the liquid was decanted from a small amount of solid material and the liquid was then diluted with water (10 mL). The precipitate was isolated by filtration to give (1.1 g, 83%) of (Z)-3-amino-2-(2,6-dimethylphenylimino)thiazolidin-4-one: mp 149-152 C.; 1H NMR (400 MHz, CDCl3) δ 7.06 (d, J=7.2 Hz, 2H), 6.98 (m, 1H), 4.75 (s, 2H), 3.80 (s, 2H), 2.12 (s, 6H); ESIMS m/z 236 (M+H).

 

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