Hydrochloric Acid → HCID 20033717, compound

HRID 231691Notes

Reaction equation

HRID 231691 reaction equation
C(S)C.[H-].[Na+].[OH:6][CH:7]([C:9]1[CH:10]=[C:11]([S:23]([NH2:26])(=[O:25])=[O:24])[S:12][C:13]=1[S:14][C:15]1[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=1)[CH3:8].Cl>CN(C=O)C>[OH:6][CH:7]([C:9]1[CH:10]=[C:11]([S:23]([NH2:26])(=[O:25])=[O:24])[S:12][C:13]=1[S:14][C:15]1[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=1)[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydride2×HCID 20033672HCID 20033672, compound

Product 1

HCID 20033717HCID 20033717, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethanethiol (2.1 ml, 0.028 mol) was added dropwise over 10 minutes to a stirred suspension of 60% NaH in mineral oil (1.28 g, 0.032 mol) in DMF (30 ml) at ice bath temperature under nitrogen. After the sodium hydride had reacted, 4-(1-hydroxyethyl)-5-(4-methoxyphenylthio)thiophene-2-sulfonamide (1.0 g, 0.0029 mol) was added and the solution was stirred at steam bath temperature over night. The mixture was cooled in ice and acidified with 3N HCl (20 ml). The mixture was extracted with ethyl acetate and the extract was washed with saturated NaCl, saturated NaHCO3 and again with saturated NaCl. The extract was dried, filtered and concentrated in vacuo. The residual oil was washed with pet ether to remove the mineral oil and was purified by silica gel chromatography using 10% methanol in chloroform. The white solid product was obtained in 61% yield, mp. 133°-137° C. Purity and structure were confirmed by HPLC, C, H, N analysis and NMR.

Workup

  1. temperatureThe mixture was cooled in ice
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated NaCl, saturated NaHCO3 and again with saturated NaCl
  4. customThe extract was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. washThe residual oil was washed with pet ether
  8. customto remove the mineral oil
  9. customwas purified by silica gel chromatography
  10. customThe white solid product was obtained in 61% yield, mp. 133°-137° C

Sources & evidence

ORD record
ord-02a5aee025b94b088d0f0cfe2e9a5a2b
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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