Ethyl chloroformate → HCID 57090489, compound

HRID 1265372Notes

Reaction equation

HRID 1265372 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][C:8]1[C:9]([Cl:27])=[CH:10][C:11]([F:26])=[C:12]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[NH:16][C:15]2=[O:25])[CH:13]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:27][C:9]1[C:8]([NH:7][C:2]([O:4][CH2:5][CH3:6])=[O:3])=[CH:13][C:12]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[NH:16][C:15]2=[O:25])=[C:11]([F:26])[CH:10]=1

Participants

5

Reactant 2

HCID 10928Ethyl chloroformateHCID 57116133HCID 57116133, compound

Product 1

HCID 57090489HCID 57090489, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl chloroformate (2.58 g) was dropwise added into a solution of 3-(5-amino-4-chloro-2-fluorophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (XLVI) in pyridine (25 ml) at 0° C., and stirred at room temperature for one hr. The reaction mixture was diluted with ethyl acetate, washed with 1N hydrochloric acid followed by water, and dried over sodium sulfate. After concentration, the crystals (5.46 g) were collected by filtration. 1H NMR (CDCl3, 300 MHz) 1.31 (3H, t, J=7.1 Hz), 4.22 (2H, q, J=7.1 Hz), 6.20 (1H, s), 7.14 (1H, br), 7.29 (1H, d, J=8.8 Hz), 7.36 (1H, d, J=6.0 Hz), 8.26 (1H, bd, J=6.4 Hz) ppm.

Workup

  1. washwashed with 1N hydrochloric acid
  2. dry with materialdried over sodium sulfate
  3. concentrationAfter concentration
  4. filtrationthe crystals (5.46 g) were collected by filtration

Sources & evidence

ORD record
ord-a43fefb9c5204c61bb96f7754031ac74
Source dataset
uspto-grants-2003_04
Patent number
US06545161B2

Reaction notes

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