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

HRID 65032Notes

Reaction equation

HRID 65032 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cc950e1f0a1b4feeaab27ac04899405e
Source dataset
uspto-grants-1986_09
Patent number
US04612321

Reaction notes

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