Butyl isocyanate → N-(Butylcarbamoyl)-3-methylthiophene-2-sulfonamide

HRID 236532

Reaction equation

HRID 236532 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[S:7]([NH2:10])(=[O:9])=[O:8].[CH2:11]([N:15]=[C:16]=[O:17])[CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:11]([NH:15][C:16]([NH:10][S:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])(=[O:9])=[O:8])=[O:17])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 3410833-Methylthiophene-2-sulfonamide

Product 1

HCID 13203354N-(Butylcarbamoyl)-3-methylthiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 150 ml of acetone and 3-methyl-2-thiophenesulfonamide was added 11 g of n-butyl isocyanate and 14 g of anhydrous potassium carbonate. After stirring at ambient temperature for 24 hours, the mixture was concentrated to 2/3 of its volume and poured into ice-water. The pH was adjusted to 3 by the addition of hydrochloric acid and the solid thus obtained was filtered, air dried and triturated with 1-chlorobutane to yield 10.6 g of N-(butylaminocarbonyl)-3-methyl-2-thiophenesulfonamide melting at 144°-146°. It showed absorption peaks by NMR (60 MC) at 2.6 δ (singlet, CH3), 1-1.8 δ (mult., C3H7), 3.42 δ (trip., N--CH2 --of butyl) and at 7.1 δ and 7.7 δ (2 doublets for CH's of thiophene) consistent for the desired structure.

Workup

  1. concentrationthe mixture was concentrated to 2/3 of its volume
  2. additionpoured into ice-water
  3. additionThe pH was adjusted to 3 by the addition of hydrochloric acid
  4. customthe solid thus obtained
  5. filtrationwas filtered
  6. customair dried
  7. customtriturated with 1-chlorobutane

Sources & evidence

ORD record
ord-dc01c366dd624bb48a108c0d84c51912
Source dataset
uspto-grants-1987_02
Patent number
US04645529

Linked notes

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