Ethyl chloroformate → HCID 19365525, compound

HRID 849945Notes

Reaction equation

HRID 849945 reaction equation
[NH2:1][C:2]1[C:3]([Cl:21])=[CH:4][C:5]([Cl:20])=[C:6]([C:8]2[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=2)[CH:7]=1.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24]>>[Cl:20][C:5]1[CH:4]=[C:3]([Cl:21])[C:2]([NH:1][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:7][C:6]=1[C:8]1[C:9](=[O:19])[N:10]([CH3:18])[C:11]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:13]=1

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 19365503HCID 19365503, compound2×

Product 1

HCID 19365525HCID 19365525, compoundYield 79%

Conditions

Temperature
100 °C

Procedure

A mixture of 0.35 g of 3-(5-amino-2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-334) and 3.1 ml of ethyl chloroformate was stirred at 100° C. for 2 hours. After completion of the reaction, the reaction mixture was left cooling to room temperature, and the excess ethyl chloroformate was distilled out under reduced pressure. The residue was recrystallized from hexane, which afforded 0.32 g (yield, 79%) of 3-(2,4-dichloro-5-ethoxycarbonylaminophenyl)-1-methyl-6-trifluoromethyl-2-oxo-1,2-dihydropyrazine (present compound 1-346; m.p., 116.2-C).

Workup

  1. customAfter completion of the reaction
  2. waitthe reaction mixture was left
  3. temperaturecooling to room temperature
  4. distillationthe excess ethyl chloroformate was distilled out under reduced pressure
  5. customThe residue was recrystallized from hexane, which

Sources & evidence

ORD record
ord-0e58a827d880489793b8875111bf1337
Source dataset
uspto-grants-2000_01
Patent number
US06015774

Reaction notes

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