Sulfolane → Methyl 10,11-dihydrodibenzo[b,f][1,4]thiazepin-3-carboxylate 5,5-Dioxide

HRID 444148Notes

Reaction equation

HRID 444148 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](=[O:18])(=[O:17])[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[N:3]=1.S1(CCCC1)(=O)=O.[BH4-].[Na+]>CCOCC>[CH:9]1[C:8]2[CH2:2][NH:3][C:4]3[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=3[S:6](=[O:18])(=[O:17])[C:7]=2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=1

Participants

5

Reactant 3

HCID 31347SulfolaneHCID 4311764Sodium borohydrideHCID 13013934HCID 13013934, compound

Product 1

HCID 13013933Methyl 10,11-dihydrodibenzo[b,f][1,4]thiazepin-3-carboxylate 5,5-Dioxide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Suspend 6.7 gm. (20 mmole) of methyl 11-chlorodibenzo[b,f][1,4]thiazepin-3-carboxylate 5,5-dioxide in 60 ml. of sulfolane and stir under nitrogen at room temperature while adding 1.52 g. (40 mmole) of sodium borohydride in small portions. Control foaming, if desired, by adding small portions of dry ether. After 2 hours, pour the reaction mixture into 300 ml. of ice-water and 75 ml. of ether. Separate the precipitate by filtration, wash with water and dry in vacuo. Dissolve the precipitate in 175 ml. of boiling acetonitrile, filter and concentrate to 100 ml. Separate the precipitate to obtain the title product. (m.p. 236° C.)

Workup

  1. additionwhile adding 1.52 g
  2. additionpour the reaction mixture into 300 ml
  3. customSeparate the precipitate
  4. filtrationby filtration
  5. washwash with water
  6. customdry in vacuo
  7. dissolutionDissolve the precipitate in 175 ml
  8. filtrationof boiling acetonitrile, filter
  9. concentrationconcentrate to 100 ml
  10. customSeparate the precipitate

Sources & evidence

ORD record
ord-61c8d991d94c4037807488847e2ed0b5
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

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