Reaction #1519111

ord-5dbb31638c184dc6bffc363a77d96fb5

Reaction equation

CCOC(=O)C(=O)c1csc(NC=O)n1
Ethyl 2-(Formylaminothiazol-4-yl)-2-oxoacetate
O=C1CCC(=O)N1Cl
N-Chlorosuccinimide
O
water
CCOC(=O)C(=O)c1nc(NC=O)sc1Cl
title intermediate
CCOC(=O)C(=O)c1nc(NC=O)sc1Cl
Ethyl 2-(2-Formylamino-5-chlorothiazol-4-yl)-2-oxoacetate

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe resulting white precipitate was filtered
  2. 2
    Washwashed with water and air
  3. 3
    Otherdried

Procedure

Ethyl 2-(Formylaminothiazol-4-yl)-2-oxoacetate (9.1 g, 39.87 mmol) (obtained from Aldrich, Milwaukee, Wis.) was slurried in 50 mL of anhydrous DMF. N-Chlorosuccinimide (5.6 g, 41.86 mmol) was added as a solid and the suspension was stirred at room temperature. After 18 hours, the reaction mixture was poured into 500 mL of water. The resulting white precipitate was filtered, washed with water and air dried to afford the title intermediate as a white solid.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07612037B2uspto-grants-2009_11