Hydrochloric Acid → 4-Ethoxycarbonyl-2-methylthiothiazole-5-carboxylic acid-tert-butylamide

HRID 5333

Reaction equation

HRID 5333 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([S:14][CH3:15])[S:9][C:10]=1[C:11](Cl)=[O:12])=[O:5])[CH3:2].[C:16]([NH2:20])([CH3:19])([CH3:18])[CH3:17].Cl>ClCCl>[C:16]([NH:20][C:11]([C:10]1[S:9][C:8]([S:14][CH3:15])=[N:7][C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:12])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 150095674-Ethoxycarbonyl-2-methylthiothiazole-5-carboxylic acid chloride

Product 1

HCID 150095734-Ethoxycarbonyl-2-methylthiothiazole-5-carboxylic acid-tert-butylamideYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.50 g (13.2 mmol) of 4-ethoxycarbonyl-2-methylthiothiazole-5-carboxylic acid chloride was dissolved in 20 ml of dichloromethane and dripped, at 0° C., into a solution of 3.20 g (44 mmol) of tert-butylamine in 50 ml of dichloromethane. The mixture was allowed to warm up to room temperature and was then stirred for 14 hours. 100 ml of 10% strength hydrochloric acid was added and the organic phase was separated, washed with 50 ml of water and dried over sodium sulfate. The solvent was removed under reduced pressure, leaving 4.00 g (100%) of product as a yellow crystalline slurry.

Workup

  1. customthe organic phase was separated
  2. washwashed with 50 ml of water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e8d6c976acfe418eb1c313ed305dfb2d
Source dataset
uspto-grants-1993_09
Patent number
US05244867

Linked notes

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