Methyl chloroformate → HCID 178502116, compound

HRID 406016Notes

Reaction equation

HRID 406016 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].Cl.[F:7][C:8]1[CH:9]=[CH:10][C:11]([N+:23]([O-:25])=[O:24])=[C:12]([CH:22]=1)[O:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20][CH3:21])[CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:5][O:4][C:2](=[O:3])[N:20]([C@H:17]1[CH2:16][CH2:15][C@H:14]([O:13][C:12]2[CH:22]=[C:8]([F:7])[CH:9]=[CH:10][C:11]=2[N+:23]([O-:25])=[O:24])[CH2:19][CH2:18]1)[CH3:21]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 178484839HCID 178484839, compound

Product 1

HCID 178502116HCID 178502116, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

129 μl methyl chloroformate were added to an ice-cooled mixture of 0.305 g [trans-4-(5-fluoro-2-nitro-phenoxy)-cyclohexyl]-methyl-amine hydrochloride and 417 μl triethylamine in 5 ml methylene chloride. After 10 minutes the coolant was removed and the mixture was stirred at rt overnight. Then the reaction mixture was diluted with methylene chloride and washed with 10% aq. potassium hydrogen sulfate solution and 10% aq.potassium carbonate solution. The organic phase was passed through a hydrophobic frit.

Workup

  1. temperaturecooled
  2. customAfter 10 minutes the coolant was removed
  3. additionThen the reaction mixture was diluted with methylene chloride
  4. washwashed with 10% aq. potassium hydrogen sulfate solution and 10% aq

Sources & evidence

ORD record
ord-46807f598dae49729f254fc3a7a17f67
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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