Hydrochloric Acid → HCID 20033703, compound

HRID 231690Notes

Reaction equation

HRID 231690 reaction equation
[CH2:1](S)[CH3:2].[H-].[Na+].OC([C:9]1[CH:13]=[C:12]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[S:11][C:10]=1[S:25]([NH2:28])(=[O:27])=[O:26])C.Cl.CN(C)C=[O:33]>>[OH:33][CH:1]([C:13]1[CH:9]=[C:10]([S:25]([NH2:28])(=[O:27])=[O:26])[S:11][C:12]=1[S:14]([C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH3:2]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6343EthanethiolHCID 24758Sodium hydride2×HCID 86743233HCID 86743233, compound

Product 1

HCID 20033703HCID 20033703, compoundYield 87%

Conditions

Temperature
80 °C

Procedure

Ethanethiol (2.1 ml, 0.028 mol) was added dropwise over a 10 minute period to a stirred suspension of 60% NaH in mineral oil (1.4 g, 0.035 mol) in dimethylformamide (50 ml) at ice bath temperature under a nitrogen atmosphere. After the sodium hydride had reacted, 4-(1-hydroxyethyl-5-(4-methoxyphenylsulfonyl)thiophene-2-sulfonamide (2.64 g, 0.007 mol) was added to the solution and the solution was heated in an oil bath at 80° C. for 31/2 hours. The solution was cooled to ice bath temperature and 3N HCl was added (20 ml). The acidic mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with saturated NaCl, saturated NaHCO3 and again with saturated NaCl, dried, filtered and concentrated in vacuo. The crude amber oil obtained was washed with pet. ether several times to remove mineral oil and was solidified by trituration in nitromethane. A white solid was obtained, 2.2 g. Recrystallization from nitromethane gave material of mp 173°-175° C. Yield 87%. Purity and structure were confirmed by HPLC, C, H, N analyses and NMR.

Workup

  1. additionwas added (20 ml)
  2. extractionThe acidic mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with saturated NaCl, saturated NaHCO3 and again with saturated NaCl
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude amber oil obtained
  9. washwas washed with pet. ether several times
  10. customto remove mineral oil
  11. customA white solid was obtained
  12. customRecrystallization from nitromethane
  13. customgave material of mp 173°-175° C

Sources & evidence

ORD record
ord-8ce66ea5332f4469a1ce0ce16681f37d
Source dataset
uspto-grants-1989_07
Patent number
US04847289

Reaction notes

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