Ammonium Hydroxide → (4-Chloro-2-nitro-5-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

HRID 498171Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12][C:13](=[O:15])C)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.[OH-:19].[NH4+]>>[C:7]([O:15][C:13](=[O:19])[NH:12][C:5]1[CH:6]=[C:7]([C:8]([F:11])([F:10])[F:9])[C:2]([Cl:1])=[CH:3][C:4]=1[N+:16]([O-:18])=[O:17])([CH3:8])([CH3:2])[CH3:6]

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 22318004N-[4-Chloro-2-nitro-5-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 69486643(4-Chloro-2-nitro-5-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

Procedure

Reaction of N-(4-chloro-2-nitro-5-trifluoromethyl-phenyl)-acetamide [CAS 157554-77-3] (4.02 g, 14.2 mmol) with Boc-anhydride (3.26 g, 14.9 mmol) according to the general procedure A (method c) and subsequent reaction with ammonium hydroxide (25%; 4.38 ml, 28.4 mmol) gave after aqueous work up and purification by column chromatography on silica gel (hexane/ethyl acetate 4:1) (4-chloro-2-nitro-5-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (3.39 g, 70%) as an orange oil.

Workup

customgave after aqueous work up
custompurification by column chromatography on silica gel (hexane/ethyl acetate 4:1) (4-chloro-2-nitro-5-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (3.39 g, 70%) as an orange oil

Sources & evidence

ORD record: ord-17d4be5fbd6645c2b05348dfe0b34497
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949542B2

Reaction notes

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