Sulfuric Acid → N-(5-amino-4-chloro-2-fluorobenzyl)-2,2,2-trifluoroacetamide

HRID 59387

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]([NH:5][CH2:6][C:7]1[C:8]([F:17])=[CH:9][C:10]([Cl:16])=[C:11]([CH:15]=1)C(O)=O)=[O:4].OS(O)(=O)=O.[N-:25]=[N+]=[N-].[Na+]>>[NH2:25][C:11]1[C:10]([Cl:16])=[CH:9][C:8]([F:17])=[C:7]([CH:15]=1)[CH2:6][NH:5][C:3](=[O:4])[C:2]([F:19])([F:18])[F:1]

Participants

Reactant 3

HCID 1118Sulfuric Acid

HCID 33557Sodium Azide

HCID 897366685-((2,2,2-Trifluoroacetamido)methyl)-2-chloro-4-fluorobenzoic acid

Product 1

HCID 90018998N-(5-amino-4-chloro-2-fluorobenzyl)-2,2,2-trifluoroacetamideYield 64,668.398%

Procedure

The title compound was prepared according to the procedure described in step-1 of Intermediate-57 by using 5-((2,2,2-trifluoroacetamido)methyl)-2-chloro-4-fluorobenzoic acid (3.0 g), conc. H2SO4 and sodium azide (0.793 g, 0.012 mmol) to afford 2.1 g of the desired product.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-069b0936d7534524b20bdb7e804dfc9b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439890B2

Linked notes

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