Hydrochloric Acid → HCID 19089322, compound

HRID 1464134Notes

Reaction equation

HRID 1464134 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:11])=[CH:5][C:6]=1[S:7]([NH2:10])(=[O:9])=[O:8].[OH-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]=[C:22]=[O:23])=[CH:17][CH:16]=1.Cl>CC(C)=O>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:10][S:7]([C:6]2[CH:5]=[C:4]([CH3:11])[S:3][C:2]=2[CH3:1])(=[O:9])=[O:8])=[O:23])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 76934-Chlorophenyl IsocyanateHCID 14798Sodium HydroxideHCID 13425729HCID 13425729, compound

Product 1

HCID 19089322HCID 19089322, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The procedure of Example 4B was followed with 2,5-dimethyl-3-thiophenesulfonamide (1.73 g, 9.06 mmole), acetone (10 ml), 1N NaOH (9.1 ml), 4-chlorophenyl isocyanate (1.39 g, 9.0 mmole), 1N HCl (9.1 ml). The aqueous layer was extracted with two 100 ml aliquots of ethyl acetate, which were combined and washed with 50 ml of water. The organic layer was then dried over Na2SO4. The solvent was removed and the residue chromatographed using a mixture of 4% methanol/methylene chloride as the eluent over a 50 mm silica gel column. The solvent was removed to provide the named product.

Workup

  1. extractionThe aqueous layer was extracted with two 100 ml aliquots of ethyl acetate, which
  2. washwashed with 50 ml of water
  3. dry with materialThe organic layer was then dried over Na2SO4
  4. customThe solvent was removed
  5. customthe residue chromatographed
  6. additiona mixture of 4% methanol/methylene chloride as the eluent over a 50 mm silica gel column
  7. customThe solvent was removed
  8. customto provide the named product

Sources & evidence

ORD record
ord-4d2c92fd541d452ab1001c730c0c3ea1
Source dataset
uspto-grants-1994_04
Patent number
US05302724

Reaction notes

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