Hydrochloric Acid → HCID 13851236, compound

HRID 978463Notes

Reaction equation

HRID 978463 reaction equation
[O:1]=[C:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][CH:8]=1.[BH4-].[Na+].Cl>C(O)C>[OH:1][CH:2]([CH3:16])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[S:11][C:10]([S:12]([NH2:15])(=[O:14])=[O:13])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 20203308HCID 20203308, compound

Product 1

HCID 13851236HCID 13851236, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(5-oxohexyl)thiophene-2-sulfonamide (1.7 g) was dissolved in ethanol and 0.2 grams of sodium borohydride added. After 1 hour of stirring the reaction mixture was made acidic with 1N hydrochloric acid then concentrated under vacuum. This residue was treated with 1N hydrochloric acid to insure that no borate esters were present. The product was then extracted into ether, dried over sodium sulfate and concentrated under vacuum to give 1.3 grams of an oil plus solid mixture. This was chromatographed twice using 230-400 mesh gel and eluting with 0-10% methanol in chloroform providing 0.6 g of product which was recrystallized from water. m.p. 75°-76° C. N.M.R. (CDCl3)δ1.16 (d, 3H), 1.43 (m, 5H), 1.64 (m, 2H), 2.80 (t, 2H), 3.76 (m, 1H), 5.04 (bs, 2H), 6.69 (d, 1H), 7.42 (d, 1H), Analysis calculated for C10H 17 NO3S2 : C, 45.60%; N, 5.32%; H, 6.51% and found: C, 45.41%; N, 5.53%; H, 6.63%.

Workup

  1. concentrationthen concentrated under vacuum
  2. additionThis residue was treated with 1N hydrochloric acid
  3. extractionThe product was then extracted into ether
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f6be7f5161da4a09bb11b4a41dbfce53
Source dataset
uspto-grants-1987_05
Patent number
US04665090

Reaction notes

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