Acetic Acid → HCID 178527189, compound

HRID 1066087Notes

Reaction equation

HRID 1066087 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]=[C:10]=S)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[S:21]([NH-:24])(=[O:23])=[O:22].C(O)(=O)C.C>C(#N)C.C(O)C>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]2[NH:13][C:10]([NH:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:24][S:21](=[O:23])(=[O:22])[C:15]=2[CH:16]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 297MethaneHCID 16741Phenethyl Isothiocyanate2×HCID 1317225932-Amino-5-chlorobenzenesulfonamide sodium salt

Product 1

HCID 178527189HCID 178527189, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

2-Phenylethyl isothiocyanate (0.36 g) was added to a stirred slurry of 2-amino-5-chlorobenzenesulfonamide sodium salt (0.50 g) in 5 ml of acetonitrile at 60° C. After 2½ h an additional amount of 2-phenylethyl isothiocyanate (0.18 g) was added, and the temperature was raised to 90° C. for 1½ h. The reaction mixture was treated with 1 ml of 4M acetic acid, 5 ml of ethanol and 0.1 g of charcoal and filtered through celite. The solvent was evaporated and the residue extracted with 10 ml of ethyl acetate. The solvent was evaporated and the oily residue was purified on a silica column eluted with ethyl acetate. The title compound was obtained as white crystals; m.p. 250-252° C.

Workup

  1. filtrationfiltered through celite
  2. customThe solvent was evaporated
  3. extractionthe residue extracted with 10 ml of ethyl acetate
  4. customThe solvent was evaporated
  5. customthe oily residue was purified on a silica column
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-ac806b2dcc2b4ea1a30039c21cbd4577
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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