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Acetyl chloride → N-[5-(2-BENZOYLAMINO-4-PYRIDYL)-4-(3,5-DIMETHYLPHENYL)-1,3-THIAZOL-2-YL]ACETAMIDE

HRID 1178595
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HRID 1178595 반응식
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[S:7][C:8]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:20]=2)=[C:9]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=2)[N:10]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[C:26]([NH:25][C:21]1[CH:20]=[C:19]([C:8]2[S:7][C:6]([NH:5][C:1](=[O:3])[CH3:2])=[N:10][C:9]=2[C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=2)[CH:24]=[CH:23][N:22]=1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1
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참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 9952828N-[4-[2-Amino-4-(3,5-dimethylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]benzamide

생성물 1

HCID 9911213N-[5-(2-BENZOYLAMINO-4-PYRIDYL)-4-(3,5-DIMETHYLPHENYL)-1,3-THIAZOL-2-YL]ACETAMIDE수율 30.1%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 31374Dimethylacetamide용매

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온도
70 °C

실험 절차

Acetyl chloride (0.26 mL, 3.7 mmol) and 4-dimethylaminopyridine (0.09 g, 0.76 mmol) were added to a solution of N-[4-[2-amino-4-(3,5-dimethylphenyl)-1,3-thiazol-5-yl]-2-pyridyl]benzamide (0.96 g, 2.4 mmol) in N,N-dimethylacetamide (20 mL) and the mixture was stirred at 70° C. for 16 hours. After the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogencarbonate (50 mL) was added. The resulting crude crystals were collected by filtration and washed with water. The crude crystals were recrystallized from ethyl acetate to obtain 0.32 g (yield 30%) of the title compound.

후처리

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationThe resulting crude crystals were collected by filtration
  3. washwashed with water
  4. customThe crude crystals were recrystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-456e231578e040c39393f24f036b1189
출처 데이터셋
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07276527B2

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