Hydrochloride methanol → Hydrochloric Acid

HRID 39155Notes

Reaction equation

HRID 39155 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1)(C)(C)C.[ClH:27].CO>>[NH2:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH:21][S:22]([CH3:25])(=[O:24])=[O:23])=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1.[ClH:27]

Participants

4

Reactant 2

HCID 21893726Hydrochloride methanolHCID 59206047[4'-(Methanesulfonylamino-methyl)-biphenyl-3-yl]-carbamic acid tert-butyl ester

Product 2

HCID 313Hydrochloric AcidYield 71%HCID 59206195N-((3'-aminobiphenyl-4-yl)methyl)methanesulfonamide

Procedure

A solution of [4′-(methanesulfonylamino-methyl)-biphenyl-3-yl]-carbamic acid tert-butyl ester (5 g, 13 mmol) in HCl/MeOH (4M, 150 mL) was stirred at room temperature overnight. The mixture was concentrated to dryness and the residue was washed with ether to give the target compound N-((3′-aminobiphenyl-4-yl)methyl)methanesulfonamide as its HCl salt (3.0 g, 71%). 1H NMR (300 MHz, DMSO-d6) δ 7.54-7.71 (m, 6H), 7.46 (d, J=7.8 Hz, 2H), 7.36 (d, J=7.5 Hz, 1H), 4.19 (s, 2H), 2.87 (s, 3H). MS (ESI) m/e (M+H+): 277.0.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. washthe residue was washed with ether

Sources & evidence

ORD record
ord-9171541f200849ac8b1928baf128888f
Source dataset
uspto-grants-2013_09
Patent number
US08524767B2

Reaction notes

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