Triethylamine → HCID 86635496, compound

HRID 1799662Notes

Reaction equation

HRID 1799662 reaction equation
[Cl:1]C(OCC)=O.[F:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([OH:26])=O.C(N(CC)CC)C>ClCCl>[F:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:15][CH2:16][O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([Cl:1])=[O:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 66874902HCID 66874902, compound

Product 1

HCID 86635496HCID 86635496, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl chloroformate (414 mg, 3.82 mmol) was added at 0° C. to a solution of 7-[2-(2,3-difluoro-phenyl)-ethoxy]-heptanoic acid (800 mg, 2.94 mmol) and triethylamine (387 mg, 3.82 mmol) in dichloromethane (15 mL), then after 2 h volatile material was removed by distillation, producing 7-[2-(2,3-difluoro-phenyl)-ethoxy]-heptanoyl chloride (855 mg). This was redissolved in acetone (2 mL) and treated at 0° C. with a solution of sodium azide (268 mg, 4.12 mmol) in water (4 mL) under vigorous stirring. The reaction mixture was stirred for 1 h at 10° C., then partitioned between toluene and brine. The organic layer was separated and heated at 65° C. for 90 min, then concentrated in vacuo, affording [6-(2,3-difluoro-benzyloxy)-hexyl]-isocyanate (486 mg, 61%) as a yellow oil.

Workup

  1. customafter 2 h volatile material was removed by distillation

Sources & evidence

ORD record
ord-4b74a75f84744e50a9caf154a65ac28e
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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