Methyl chloroformate → HCID 86694143, compound

HRID 707271Notes

Reaction equation

HRID 707271 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[NH:4][CH3:5].C(N(C(C)C)CC)(C)C.Cl[C:20]([O:22][CH3:23])=[O:21]>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[N:4]([CH3:5])[C:20](=[O:21])[O:22][CH3:23]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 3340862-Bromo-N-methylaniline

Product 1

HCID 86694143HCID 86694143, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-N-methylaniline (1.00 g, 5.37 mmol) and diisopropylethylamine (2.0 ml, 11.50 mmol) were dissolved in dichloromethane (50 mL) and cooled in an ice bath. Methyl chloroformate (1.0 ml, 12.94 mmol) was added dropwise and the reaction stirred overnight. The reaction mixture was partitioned between water (200 mL) and ethyl acetate (200 mL). The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude was used without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customThe reaction mixture was partitioned between water (200 mL) and ethyl acetate (200 mL)
  3. dry with materialThe organic was dried with magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customThe crude was used without further purification

Sources & evidence

ORD record
ord-887f92b217ca4d89b5ce8d45b9ce48b8
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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