Hydrochloric Acid → 1-[4-(Methanesulfonyl)phenyl]-2-nitroethan-1-one

HRID 1864167Notes

Reaction equation

HRID 1864167 reaction equation
CC(C)([O-])C.[K+].[CH3:7][N+:8]([O-:10])=[O:9].C1([O:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)C=CC=CC=1.NC(N)=O.Cl>CS(C)=O.O>[CH3:28][S:25]([C:22]1[CH:23]=[CH:24][C:19]([C:18](=[O:17])[CH2:7][N+:8]([O-:10])=[O:9])=[CH:20][CH:21]=1)(=[O:26])=[O:27]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1176UreaHCID 6375NitromethaneHCID 2671347HCID 2671347, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 218977141-[4-(Methanesulfonyl)phenyl]-2-nitroethan-1-oneYield 75.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a suspension of potassium tert-butoxide (24.3 g, 217.1 mmol) in DMSO (150 mL), was added CH3NO2 (11.7 mL, 217.1 mmol) added at 0° C. After stirring for 1 h, 4-methanesulfonyl-benzoic acid phenyl ester (20.0 g, 72.4 mmol) was added in one portion at 0° C. The reaction was warmed to room temperature and stirred for 5 hr. The reaction was poured into ice-water (200 mL) and followed by adding urea (2.17 g, 36.2 mmol). The reaction was acidified with 5.0M HCl to pH=5 at 0° C. The reaction was added to water (1L) and stirred for 1 h. The pale yellow solid was filtered and dried under vacuum to afford the desired compound (13.2 g, 75.2%). 1H NMR (400Mz, DMSO-d6) δ 8.19 (m, 4H), 6.63 (s, 2H), 3.35 (s, 3H). LCMS 244.5 [M+H].

Workup

  1. additionadded at 0° C
  2. stirringstirred for 5 hr
  3. stirringstirred for 1 h
  4. filtrationThe pale yellow solid was filtered
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f3ef7333a9084f899123f1888309a203
Source dataset
uspto-grants-2009_12
Patent number
US07625906B2

Reaction notes

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