Hydrochloric Acid → HCID 884458, compound

HRID 1982282Notes

Reaction equation

HRID 1982282 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:12][N:13]([CH3:18])[S:14](Cl)(=[O:16])=[O:15].Cl>N1C=CC=CC=1>[CH3:12][N:13]([CH3:18])[S:14]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12082Methyl 4-aminobenzoateHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 884458HCID 884458, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 8.5 g of methyl 4-aminobenzoate 13 and 43 ml of pyridine is added 12.1 g of dimethylsulfamoyl chloride, and the mixture is stirred at 50° C. for 2 hours. The reaction mixture to which is added ice-water is acidified with 6N hydrochloric acid and extracted with methylene chloride. The organic layer is washed with water, dried, and concentrated under reduced pressure. The residue is washed with ether-isopropyl ether to give 9.5 g (yield: 65.4%) of methyl 4-(dimethylaminosulfonyl)aminobenzoate 14.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic layer is washed with water
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. washThe residue is washed with ether-isopropyl ether

Sources & evidence

ORD record
ord-edd99833a7c34631951ba1bf7a3d51d9
Source dataset
uspto-grants-1986_06
Patent number
US04595780

Reaction notes

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