Dimethylamine → Methyl 3-[(dimethylamino)sulfonyl]-2-methylbenzoate

HRID 648855Notes

Reaction equation

HRID 648855 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[S:12](Cl)(=[O:14])=[O:13].[CH3:16][NH:17][CH3:18]>O1CCCC1>[CH3:1][C:2]1[C:3]([S:12]([N:17]([CH3:18])[CH3:16])(=[O:14])=[O:13])=[CH:4][CH:5]=[CH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 139376413-(CHLOROSULFONYL)-2-METHYLBENZOIC ACID METHYL ESTER

Product 1

HCID 13937642Methyl 3-[(dimethylamino)sulfonyl]-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 33.5 g of the product from Example 9 in 300 ml tetrahydrofuran was cooled to 5°-10° and treated with dimethylamine. The resulting suspension was stirred at room temperature for one hour, filtered, and the filtrate concentrated in vacuo to afford a pale yellow solid. Recrystallization from n-butyl chloride gave 26.7 g of the title compound as a white solid, m.p. 40°-43°; NMR (CDCl3): δ 2.75 (3H, s, CH3), 2.8 (6H, s, SO2N(CH3)2), 3.85 (3H, s, CO2CH3), 7.25-7.55 (1H, m), 7.85-8.25 (2H, m).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto afford a pale yellow solid
  4. customRecrystallization from n-butyl chloride

Sources & evidence

ORD record
ord-a3654b96a8884749b6091029b1d70356
Source dataset
uspto-grants-1988_04
Patent number
US04737185

Reaction notes

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