2-Mercaptoethanol → 4-[(2-Hydroxyethyl)sulfanyl]benzenesulfonamide

HRID 2118576Notes

Reaction equation

HRID 2118576 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[H-].[Na+].CN(C)C=[N:10][S:11]([C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1)(=[O:13])=[O:12]>CN(C=O)C>[OH:4][CH2:3][CH2:2][S:1][C:17]1[CH:18]=[CH:19][C:14]([S:11]([NH2:10])(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 24758Sodium hydrideHCID 53649348HCID 53649348, compound

Product 1

HCID 42697544-[(2-Hydroxyethyl)sulfanyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-mercaptoethanol (58.6 g, 0.75 mol) in freshly degassed DMF (100 mL) was added dropwise under N2 to a stirred mixture of NaH (34.5 g, 50% oil suspension, 0.75 mol) and DMF (400 mL). When gas evolution was complete, N,N-dimethyl-N'-(4-bromobenzenesulfonyl)formamidine (146 g, 0.50 mol) was added and the mixture was heated on the steam bath for one hour. The DMF was removed in vacuo and methanol (500 mL) and 10% (w/v) aqueous NaOH solution (500 mL) was added to the residue. This solution was warmed on the steam bath for one hour and the methanol removed. The residue was diluted with water (2500 mL) and washed with petroleum ether. The separated aqueous layer was acidified with concentrated HCl. The white solid that separated was filtered, washed with water and dried. Extraction of the aqueous filtrate with ethyl acetate produced an additional quantity of product; total yield, 112.4 g; mp 103°-108° C. Recrystallization of a sample from water followed by recrystallization from dichloroethane gave material with mp 111°-112° C.

Workup

  1. temperaturethe mixture was heated on the steam bath for one hour
  2. customThe DMF was removed in vacuo and methanol (500 mL) and 10% (w/v) aqueous NaOH solution (500 mL)
  3. additionwas added to the residue
  4. temperatureThis solution was warmed on the steam bath for one hour
  5. customthe methanol removed
  6. additionThe residue was diluted with water (2500 mL)
  7. washwashed with petroleum ether
  8. customThe white solid that separated
  9. filtrationwas filtered
  10. washwashed with water
  11. customdried
  12. extractionExtraction of the aqueous filtrate with ethyl acetate
  13. customproduced an additional quantity of product
  14. customRecrystallization of a sample from water
  15. customfollowed by recrystallization from dichloroethane
  16. customgave material with mp 111°-112° C.

Sources & evidence

ORD record
ord-220e36c976464756abe9a7be3f8e3ec9
Source dataset
uspto-grants-1987_07
Patent number
US04678855

Reaction notes

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