Dimethylcarbamoyl Chloride → 2-Dimethylcarbamoyloxy-5-methanesulfonyl-benzoic acid benzyl ester

HRID 1820762Notes

Reaction equation

HRID 1820762 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[C:10]1[CH:15]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:13]=[CH:12][C:11]=1[OH:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.[CH3:29][N:30]([CH3:34])[C:31](Cl)=[O:32]>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:1]([O:8][C:9](=[O:21])[C:10]1[CH:15]=[C:14]([S:16]([CH3:19])(=[O:17])=[O:18])[CH:13]=[CH:12][C:11]=1[O:20][C:31](=[O:32])[N:30]([CH3:34])[CH3:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 79724-MethylmorpholineHCID 69037381HCID 69037381, compound

Product 1

HCID 690360752-Dimethylcarbamoyloxy-5-methanesulfonyl-benzoic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1 mmol 2-hydroxy-5-methanesulfonyl-benzoic acid benzyl ester, 1.5 mmol of N-methylmorpholine and 0.2 mmol of 4-dimethylaminopyridine in 4 ml of dimethylformamide was treated with 1.3 mmol of N,N-dimethyl-carbamoylchloride. The reaction mixture was stirred at 60° for 48 hours, concentrated in vacuo and the residue taken up in 5 ml of water. Acidification with diluted hydrochloric acid and extraction with ethyl acetate yielded a crude product which was purified by chromatography (SiO2; ethyl acetate/cyclohexane 1.1). MS (m/e): 378.3 (MH+, 100%)

Workup

  1. concentrationconcentrated in vacuo
  2. extractionAcidification with diluted hydrochloric acid and extraction with ethyl acetate

Sources & evidence

ORD record
ord-bbfbc4808c67429d816de44a5b14b897
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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