Triethylamine → 2-Amino-N-benzyloxy-3,4,5,6-tetrafluoro-benzamide

HRID 2270243Notes

Reaction equation

HRID 2270243 reaction equation
[NH2:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([F:14])[C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH2:28]([O:35][NH2:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>C1COCC1>[NH2:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([F:14])[C:3]=1[C:4]([NH:36][O:35][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 102312Benzyloxyamine hydrochlorideHCID 6881852-Amino-3,4,5,6-tetrafluorobenzoic acid

Product 1

HCID 226328792-Amino-N-benzyloxy-3,4,5,6-tetrafluoro-benzamideYield 106.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure for Example A, 2-amino-3,4,5,6-tetrafluorobenzoic acid (3.0 g, 14.4 mmol) was reacted with carbonyldiimidazole (2.8 g, 17.2 mmol), O-benzylhydroxylamine hydrochloride (3.44 g, 21.5 mmol), and triethylamine (3.0 mL, 21.5 mmol) in THF (50 mL) to provide 4.8 g of the title compound.

Sources & evidence

ORD record
ord-1e111692dc1f4504957b08aba6a257cf
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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