Dimethylformamide → HCID 117779798, compound

HRID 2272920Notes

Reaction equation

HRID 2272920 reaction equation
[Na].[CH2:2]([SH:4])[CH3:3].[CH2:5]([O:7][C:8]([C:10]1[N:11]=[CH:12][S:13][C:14]=1Cl)=[O:9])[CH3:6].CN(C=O)C.C1COCC1>O>[CH2:5]([O:7][C:8]([C:10]1[N:11]=[CH:12][S:13][C:14]=1[S:4][CH2:2][CH3:3])=[O:9])[CH3:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 45051917Sodium ethanethiolHCID 58758599Ethyl 5-chloro-1,3-thiazole-4-carboxylate

Product 1

HCID 117779798HCID 117779798, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.56 g of ethyl mercaptan sodium salt (80%) was added to a mixture of 0.86 g of 5-chlorothiazole-4-carboxylic acid ethyl ester, 3 ml of DMF and 1 ml of THF, under ice cooling, and then the mixture was stirred at room temperature for 1 hour. Water was poured to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.71 g of 5-ethylsulfanylthiazole-4-carboxylic acid ethyl ester.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-00f52ef3be9744b28cfadf1242cfa69c
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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