Ethyl chloroformate → Ethyl (4-bromo-2-cyanophenyl)carbamate

HRID 1786101Notes

Reaction equation

HRID 1786101 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[C:4]#[N:5].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13]>>[CH2:15]([O:14][C:12](=[O:13])[NH:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[C:4]#[N:5])[CH3:16]

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 4297402-Amino-5-bromobenzonitrile

Product 1

HCID 18367857Ethyl (4-bromo-2-cyanophenyl)carbamateYield 68%

Procedure

A suspension of 2-amino-5-bromobenzonitrile (58.5 g, 297 mmol) in ethyl chloroformate (141 mL, 1.48 mol) was heated at reflux for 5 h. The excess ethyl chloroformate (99 mL) was distilled off and toluene (96 mL) was added. Slow addition of cyclohexane (228 mL) induced crystallization. The resulting solid was collected by filtration and rinsed with cyclohexane. Drying in vacuo afforded the title compound (54.3 g, 68%) as an orange solid. MS: m/e=267.1/269.2 [M—H−].

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. distillationThe excess ethyl chloroformate (99 mL) was distilled off
  4. additiontoluene (96 mL) was added
  5. additionSlow addition of cyclohexane (228 mL)
  6. customcrystallization
  7. filtrationThe resulting solid was collected by filtration
  8. washrinsed with cyclohexane
  9. customDrying in vacuo

Sources & evidence

ORD record
ord-c226dfd0b3a249e6993d3cfb1ff6271d
Source dataset
uspto-grants-2009_03
Patent number
US07507728B2

Reaction notes

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