Ethyl chloroformate → HCID 54532145, compound

HRID 1590038Notes

Reaction equation

HRID 1590038 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[NH2:7][N:8]1[CH2:14][CH:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C:12]2[CH:26]=[CH:27][CH:28]=[CH:29][C:11]=2[CH2:10][CH2:9]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:5]([O:4][C:2](=[O:3])[NH:7][N:8]1[CH2:14][CH:13]([O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]([F:23])([F:24])[F:25])=[CH:20][CH:21]=2)[C:12]2[CH:26]=[CH:27][CH:28]=[CH:29][C:11]=2[CH2:10][CH2:9]1)[CH3:6]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 19769424HCID 19769424, compound

Product 1

HCID 54532145HCID 54532145, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl chloroformate (3.6 g) in 25 ml dichloromethane was slowly added to a solution of 3-amino-2,3,4,5-tetrahydro-1-(4-trifluoromethylphenoxy)-3-benzazepine (9 g) in 100 ml dichloromethane containing sodium bicarbonate (7 g). After one hour, the reaction mixture was filtered and concentrated to 11 g solid. A 3 g sample was recrystallized from ether to yield 2.2 g white crystals, mp 156°-157°.

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated to 11 g solid
  3. customA 3 g sample was recrystallized from ether

Sources & evidence

ORD record
ord-ebd8f46e2bd74042bc690e197e769f42
Source dataset
uspto-grants-1993_04
Patent number
US05202319

Reaction notes

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