Methyl chloroformate → HCID 12453840, compound

HRID 1967167Notes

Reaction equation

HRID 1967167 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][O:18][C:19](Cl)=[O:20]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:19](=[O:20])[O:18][CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 775714-Bromobenzylamine

Product 1

HCID 12453840HCID 12453840, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-bromophenyl)methanamine (300 mg, 1.612 mmol) was taken up in dichloromethane (8062 μl) and triethylamine (225 μl, 1.612 mmol) was added. The solution was cooled to 0° C. and methyl chloridocarbonate (118 μl, 1.612 mmol) was added dropwise. The reaction was allowed to warm to room temperature overnight. It was quenched with aqueous sodium bicarbonate and extracted using ethyl acetate (3×). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Purification was performed via silica gel chromatography (50-100% ethyl acetate in hexanes) to yield the title compound.

Workup

  1. temperatureto warm to room temperature overnight
  2. customIt was quenched with aqueous sodium bicarbonate
  3. extractionextracted
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification

Sources & evidence

ORD record
ord-fa7cfdac557745bf8f10ab172a339c93
Source dataset
uspto-grants-2013_04
Patent number
US08420695B2

Reaction notes

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