Ammonium Hydroxide → 4-[(Methylsulfonyl)amino]butanamide

HRID 1955036Notes

Reaction equation

HRID 1955036 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][NH:8][S:9]([CH3:12])(=[O:11])=[O:10])C.[NH4+:14].[OH-]>>[CH3:12][S:9]([NH:8][CH2:7][CH2:6][CH2:5][C:4]([NH2:14])=[O:3])(=[O:11])=[O:10]

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 53959923Ethyl 4-[(methylsulfonyl)amino]butanoate

Product 1

HCID 222467414-[(Methylsulfonyl)amino]butanamide

Procedure

A solution of 4-methanesulfonylamino-butyric acid ethyl ester (7.08 g, 33.8 mmol) in concentrated NH4OH (200 mL) was stirred at room temperature for 66 h. The reaction mixture was concentrated to afford the title compound of Step B as a white solid (6.16 g). The product was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 3.30 (s, 3H), 3.05-3.09 (m, 2H), 2.91 (s, 3H), 2.24-2.30 (m, 2H), 1.80-1.85 (m, 2H); MS 181 (M+ +1).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1bb08bf6b17e480f9a93ab2f668edf27
Source dataset
uspto-grants-2000_09
Patent number
US06124314

Reaction notes

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