Benzoyl chloride → tert-Butyl benzoyloxycarbamate

HRID 1475970Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([NH:17][OH:18])=[O:16])([CH3:13])([CH3:12])[CH3:11]>>[C:1]([O:18][NH:17][C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 97534tert-butyl N-hydroxycarbamate

Product 1

HCID 10037153tert-Butyl benzoyloxycarbamate

Procedure

[(tert-Butoxy)carbonyl]amino benzoate is prepared from benzoyl chloride and N-tert-butoxycarbonyl hydroxylamine according to Scheme 1 described by Carpino et al. J. Am. Chem. Soc. 1959, 955-957. (7.2 g, 80%), 1H NMR (250 MHz, DMSO-d6) δ ppm 10.89 (1H, br. s.), 7.90-8.12 (2H, m), 7.68-7.82 (1H, m), 7.51-7.65 (2H, m), 1.43 (9H, s).

Sources & evidence

ORD record: ord-246e88cf79d44bb89dca4e21efbc04fa
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018411B2

Reaction notes

Loading…