Water → 4-acetamino-3-methyl-N-(beta-methanesulfonamidoethyl)-N-ethylaniline

HRID 436545

Reaction equation

HRID 436545 reaction equation
[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([NH:9][CH2:10][CH3:11])=[CH:7][C:6]=1[CH3:14])[C:2]([CH3:4])=[O:3].[CH3:15][S:16]([NH:19][CH2:20][CH2:21]Cl)(=[O:18])=[O:17].C(=O)([O-])O.[Na+].O>CO>[NH:1]([C:5]1[CH:13]=[CH:12][C:8]([N:9]([CH2:21][CH2:20][NH:19][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:10][CH3:11])=[CH:7][C:6]=1[CH3:14])[C:2]([CH3:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 89092N-(2-Chloroethyl)methanesulphonamideHCID 516892Sodium BicarbonateHCID 214528314-Acetamino-3-methyl-N-ethylaniline

Product 1

HCID 214528344-acetamino-3-methyl-N-(beta-methanesulfonamidoethyl)-N-ethylaniline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 57.6g of 4-acetamino-3-methyl-N-ethylaniline, 52g of βmethanesulfonamidoethyl chloride, 27.7g of sodium hydrogen carbonate, 70g of water and 70ml of methanol were refluxed for 5 hours, and thereafter the methanol was distilled out under reduced pressure. Water was added to the reaction system and an oily product separated out. This oily product was poured into ethyl acetate and cooled to obtain white 4-acetamino-3-methyl-N-(β-methanesulfonamidoethyl)-N-ethylaniline.

Workup

  1. temperaturewere refluxed for 5 hours
  2. distillationthe methanol was distilled out under reduced pressure
  3. additionWater was added to the reaction system
  4. customan oily product separated out
  5. additionThis oily product was poured into ethyl acetate
  6. temperaturecooled

Sources & evidence

ORD record
ord-0415ffa5af224365b1f5a0fffd76f923
Source dataset
uspto-grants-1977_02
Patent number
US04009205

Linked notes

Loading…