Hydrochloric Acid → N-(n-butyl)sulfonylurea

HRID 1262969Notes

Reaction equation

HRID 1262969 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=CC=1CC(OC)=O)(=[O:4])=[O:3].C([N:20]=[C:21]=[O:22])CCC.C(=O)([O-])[O-].[K+].[K+].Cl>C(C(C)=O)C>[CH2:5]([S:2]([NH:1][C:21]([NH2:20])=[O:22])(=[O:3])=[O:4])[CH2:10][CH2:9][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 13064551Methyl 2-(2-sulfamoylphenyl)acetate

Product 1

HCID 21473173N-(n-butyl)sulfonylureaYield 135%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 22.9 g methyl o-aminosulfonylbenzeneacetate, 13.5 g n-butyl isocyanate, 15.2 g potassium carbonate and 250 ml methyl ethyl ketone was stirred and refluxed for three hours. The reaction mixture was cooled, poured into 1250 g of ice-water, and acidified to pH 1.5 with concentrated HCl. The product was filtered, washed and dried. The crude product was recrystallized from 1-chlorobutane to yield 24.3 g of purified N-(n-butyl)sulfonylurea derivative of methyl o-isocyanatosulfonylbenzeneacetate, m.p. 164°-166° (dec.).

Workup

  1. temperaturerefluxed for three hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe product was filtered
  4. washwashed
  5. customdried
  6. customThe crude product was recrystallized from 1-chlorobutane

Sources & evidence

ORD record
ord-80b65c14d7754c0297a77594732a3bbb
Source dataset
uspto-grants-1984_06
Patent number
US04454335

Reaction notes

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