Ethyl 3-chloro-3-oxopropionate → 2-Ethoxycarbonylacetylamino-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole

HRID 65032

반응식

HRID 65032 반응식
[NH2:1][C:2]1[S:3][C:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:6]=1.[CH2:21]([O:23][C:24]([CH2:26][C:27](Cl)=[O:28])=[O:25])[CH3:22].Cl.[Na]>CN(C)C=O>[CH2:21]([O:23][C:24]([CH2:26][C:27]([NH:1][C:2]1[S:3][C:4]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:6]=1)=[O:28])=[O:25])[CH3:22]

참가 물질

5

반응물 3

HCID 118931Ethyl 3-chloro-3-oxopropionateHCID 30248942-Thiazolamine, 4-(4-methoxyphenyl)-5-(3-pyridinyl)-HCID 23872008Sodium hydrochloride

생성물 1

HCID 98009472-Ethoxycarbonylacetylamino-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole수율 61%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

In 5 ml of dimethylformamide was dissolved 1 g of 2-amino-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole. To the solution was added under ice-cooling 580 mg of ethoxycarbonylacetylchloride. The mixture was stirred for 30 minutes, to which was then added a saturated aqueous solution of sodium hydrogen chloride. The resultant was subjected to extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated, followed by recrystallization from tetrahydrofuran to give 850 mg (61%) of 2-ethoxycarbonylacetylamino-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole, m.p. 202°-203° C.

후처리

  1. additionTo the solution was added under ice-
  2. extractionThe resultant was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customfollowed by recrystallization from tetrahydrofuran

출처 및 근거

ORD 기록
ord-cc950e1f0a1b4feeaab27ac04899405e
출처 데이터셋
uspto-grants-1986_09
특허 번호
US04612321

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