Sulfolane → HCID 13013927, compound

HRID 444141Notes

Reaction equation

HRID 444141 reaction equation
Cl[C:2]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([O:15][CH3:16])=[O:14])=[CH:12][C:7]=2[S:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]=2[N:3]=1.S1(=O)(=O)CCCC1.[BH4-].[Na+]>>[CH:9]1[C:8]2[CH2:2][NH:3][C:4]3[CH:20]=[CH:19][CH:18]=[CH:17][C:5]=3[S:6][C:7]=2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=1

Participants

4

Reactant 3

HCID 31347SulfolaneHCID 4311764Sodium borohydride2×HCID 13013926HCID 13013926, compound

Product 1

HCID 13013927HCID 13013927, compound

Procedure

Suspend 3.035 gm. (10 mmole) of methyl 11-chlorodibenzo[b,f][1,4]thiazepin-3-carboxylate in 30 ml. of solfolane (tetrahydrothiophene 1,1-dioxide) and add 766 mg. (20 mmole) of sodium borohydride in small portions with stirring. Stir at room temperature for 3 hours, add a further 190 mg. (5 mmole) of sodium borohydride and continue stirring for 1 hour. Pour the reaction mixture into 100 ml. of ice-water. Extract with three 50 ml. portions of dry ether. Wash the ether extract twice with 50 ml. portions of saturated aqueous sodium chloride, dry over magnesium sulfate and evaporate to a residue. Chromatograph the residue over 100 gm. of silica gel eluting with 1:9 ethyl acetate in toluene. Recrystallize the recovered product from acetonitrile to obtain the title product. (m.p. 149°-150° C.).

Workup

  1. additionadd a further 190 mg
  2. additionPour the reaction mixture into 100 ml
  3. extractionExtract with three 50 ml
  4. washWash the ether
  5. extractionextract twice with 50 ml
  6. dry with materialportions of saturated aqueous sodium chloride, dry over magnesium sulfate
  7. customevaporate to a residue
  8. customRecrystallize the recovered product from acetonitrile

Sources & evidence

ORD record
ord-1a1c4f527a894a82bad28cfd8b79c638
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

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