Methyl chloroformate → HCID 4629173, compound

HRID 439287Notes

Reaction equation

HRID 439287 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.C(N(CC)CC)C.Cl[C:21]([O:23][CH3:24])=[O:22]>ClCCl>[CH3:24][O:23][C:21]([NH:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1)=[O:22]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylate

Product 1

HCID 4629173HCID 4629173, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.0g of ethyl 2-amino-4-methyl-thiazole-5-carboxylate and 2.7ml of triethylamine were dissolved in 40ml of dichloromethane and then 1.1ml of methyl chloroformate was added thereto at 0° C. The reaction mixture was stirred for 6 hours at normal temperature, evaporated to remove the solvent and then extracted with 10% aqueous sodium hydroxide solution and ethylacetate. The organic layer was separated, dried over anhydrous magnesium sulfate and then evaporated to obtain 2.1g (Yield 81%) of ethyl 2-methoxycarbonylamino-4-methyl-thiazole-5-carboxylate as a pale yellow solid. The resulting product was hydrolyzed according to the same procedure as PREPARATION 1 to obtain 1.4g (Yield 75%) of the title compound as a pale yellow solid.

Workup

  1. customat 0° C
  2. customevaporated
  3. customto remove the solvent
  4. extractionextracted with 10% aqueous sodium hydroxide solution and ethylacetate
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-8f733e14cebf456db8e872221903fa2a
Source dataset
uspto-grants-1996_05
Patent number
US05514643

Reaction notes

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