Butyl isocyanate → N-(Butylcarbamoyl)-4-methylthiophene-3-sulfonamide

HRID 236526Notes

Reaction equation

HRID 236526 reaction equation
[CH3:1][C:2]1[C:3]([S:7]([NH2:10])(=[O:9])=[O:8])=[CH:4][S:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:17]([N:21]=[C:22]=[O:23])[CH2:18][CH2:19][CH3:20]>C(C(C)=O)C>[CH2:17]([NH:21][C:22]([NH:10][S:7]([C:3]1[C:2]([CH3:1])=[CH:6][S:5][CH:4]=1)(=[O:9])=[O:8])=[O:23])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 5660444-Methylthiophene-3-sulfonamide

Product 1

HCID 13203330N-(Butylcarbamoyl)-4-methylthiophene-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

4-Methyl-3-thiophenesulfonamide (22 g), 125 ml of methyl ethyl ketone, 16.6 g of potassium carbonate and 14.3 g of butyl isocyanate was stirred at reflux for six hours, allowed to stand overnight and then evaporated to a syrup. Water (150 ml) was added to the residue and the mixture was filtered to remove a small amount of solid. The filtrate was acidified, cooled and the resulting intermediate was filtered off. It melted at 126°-131° C.

Workup

  1. temperatureat reflux for six hours
  2. customevaporated to a syrup
  3. additionWater (150 ml) was added to the residue
  4. filtrationthe mixture was filtered
  5. customto remove a small amount of solid
  6. temperaturecooled
  7. filtrationthe resulting intermediate was filtered off

Sources & evidence

ORD record
ord-703ea3e4ba974a3ebfba4a964c71e9ee
Source dataset
uspto-grants-1987_02
Patent number
US04645529

Reaction notes

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