Ethyl chloroformate → Ethyl-4-chloro-5-formyl-2,3,6,7-tetrahydro-1H-1-azepine carboxylate

HRID 1648926Notes

Reaction equation

HRID 1648926 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].C([N:14]1[CH2:20][CH2:19][C:18]([CH:21]=[O:22])=[C:17]([Cl:23])[CH2:16][CH2:15]1)C1C=CC=CC=1>C(Cl)Cl>[CH2:5]([O:4][C:2]([N:14]1[CH2:20][CH2:19][C:18]([CH:21]=[O:22])=[C:17]([Cl:23])[CH2:16][CH2:15]1)=[O:3])[CH3:6]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 130720301-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepine-4-carbaldehyde

Product 1

HCID 13072034Ethyl-4-chloro-5-formyl-2,3,6,7-tetrahydro-1H-1-azepine carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3.6 gm (0.033 mol) of ethyl chloroformate in 15 ml of dry methylene chloride was added dropwise at room temperature, while stirring, within 30 minutes to a solution of 7.5 gm (0.03 mol) of 1-benzyl-4-chloro-5-formyl-2,3,6,7-tetrahydro-1H-azepine in 50 ml of dry methylene chloride, whereupon the temperature of the reaction mixture increased from 22° C. to 27° C. After the addition was complete, the mixture was stirred at room temperature for another 3 hours. Then, the methylene chloride was distilled off in a rotary evaporator, and the residue was distilled in a high vacuum.

Workup

  1. temperatureincreased from 22° C. to 27° C
  2. additionAfter the addition
  3. distillationThen, the methylene chloride was distilled off in a rotary evaporator
  4. distillationthe residue was distilled in a high vacuum

Sources & evidence

ORD record
ord-3877fb6d62984d059df3775629f9e5ca
Source dataset
uspto-grants-1983_11
Patent number
US04414225

Reaction notes

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