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

HRID 890799Notes

Reaction equation

HRID 890799 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 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-a001c871006545d09c7f9c10087a59ab
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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