Chlorosulfonyl isocyanate → 2-Methyl-5-ureido-thiazole-4-carboxylic acid ethyl ester

HRID 1365835Notes

Reaction equation

HRID 1365835 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:12])[S:9][C:10]=1[NH2:11])=[O:5])[CH3:2].ClS([N:17]=[C:18]=[O:19])(=O)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH3:12])[S:9][C:10]=1[NH:11][C:18]([NH2:17])=[O:19])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 13329095Ethyl 5-amino-2-methylthiazole-4-carboxylate

Product 1

HCID 582349302-Methyl-5-ureido-thiazole-4-carboxylic acid ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-methyl-thiazole-4-carboxylic acid ethyl ester (15.0 g, 0.081 mol) in DCM (550 mL) was added chlorosulfonyl isocyanate (8.92 mL, 0.102 mol) dropwise at −78° C. The thick suspension was allowed to warm to RT and stirred for 45 minutes. The resulting precipitate was collected by filtration and dried in vacuo. The resultant white solid was suspended in an aqueous solution of HCl (6 M, 400 mL) and heated at 90° C. for 1 h. The resulting solution was cooled to 0° C. and pH adjusted to 5 with an aqueous solution of NaOH (6 M). The resultant precipitate was collected by filtration and dried in vacuo at 60° C. for 36 h to give the title compound (16.4 g, 89%).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried in vacuo
  3. temperatureheated at 90° C. for 1 h
  4. temperatureThe resulting solution was cooled to 0° C.
  5. filtrationThe resultant precipitate was collected by filtration
  6. customdried in vacuo at 60° C. for 36 h

Sources & evidence

ORD record
ord-76dc3c4e28194b63a55c2a7125d12baa
Source dataset
uspto-grants-2011_02
Patent number
US07893060B2

Reaction notes

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