Oxalyl chloride → 6-Chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanate

HRID 59341Notes

Reaction equation

HRID 59341 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([F:11])[C:5]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.C(Cl)(=O)[C:21](Cl)=[O:22]>C(Cl)CCl>[Cl:1][C:2]1[C:7]([C:8]([N:10]=[C:21]=[O:22])=[O:9])=[C:6]([F:11])[C:5]([CH2:12][NH:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:18])[CH3:17])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 900195026-Chloro-2-fluoro-3-(pivalamidomethyl)benzamide

Product 1

HCID 900197456-Chloro-2-fluoro-3-(pivalamidomethyl)benzoyl isocyanateYield 307.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 6-chloro-2-fluoro-3-(pivalamidomethyl)benzamide (0.300 g, 1.04 mmol) in EDC (10 mL) was added oxalyl chloride (0.11 mL, 1.25 mmol). The reaction mass was heated at 60-70° C. for 4-5 h. Excess of solvent was removed under vacuum to afford 1.0 g of desired product.

Workup

  1. customExcess of solvent was removed under vacuum

Sources & evidence

ORD record
ord-a8c9d7c9b3314fe6945cfa1466867455
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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