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

HRID 65032

反応式

HRID 65032 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cc950e1f0a1b4feeaab27ac04899405e
出典データセット
uspto-grants-1986_09
特許番号
US04612321

関連ノート

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