(Dimethyl sulfide)trihydroboron → HCID 70060990, compound

HRID 362334Notes

Reaction equation

HRID 362334 reaction equation
[CH3:1][N:2]([CH3:22])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[NH:12][C:11](=O)[C:10]=2[CH:21]=1)(=[O:5])=[O:4].B.CSC>O1CCCC1.CO>[CH3:1][N:2]([CH3:22])[S:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[NH:12][CH2:11][C:10]=2[CH:21]=1)(=[O:4])=[O:5]

Participants

5

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 53754068HCID 53754068, compound

Product 1

HCID 70060990HCID 70060990, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To 5.88 g of 10,11-dihydro-N,N-dimethyl-11-oxodibenz[b,f][1,4]oxazepine-2-sulfonamide in 5 ml of tetrahydrofuran is added 20 ml of a molar solution of borane-dimethylsulfide in tetrahydrofuran. The mixture is stirred overnight and then refluxed for 2 hours. The mixture is chilled, diluted with 10 ml of methanol and then concentrated, methanol added again and the mixture concentrated. To the mixture is added 20 ml of 2N NaOH and the mixture refluxed for 2 hours. The mixture is extracted with dichloromethane, the extract dried (MgSO4) and filtered. The filtrate is passed through a thin pad of hydrous magnesium silicate and the pad washed with dichloromethane. The filtrate is concentrated to give 4.8 g of crystals, m.p. 99°-102° C. Recrystallization from diisopropylether-dichloro-methane gives 3.96 g of crystals, m.p. 109°-110° C. Mass Spectrum (FAB) 305(M+H). Anal. Calc'd for C15H16N2O3S: C,59.2; H,5.3; N,9.2; S,10.6. Found: C,57.6; H,5.2; N,8.9; S,10.1.

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureThe mixture is chilled
  3. concentrationconcentrated
  4. additionmethanol added again
  5. concentrationthe mixture concentrated
  6. additionTo the mixture is added 20 ml of 2N NaOH
  7. temperaturethe mixture refluxed for 2 hours
  8. extractionThe mixture is extracted with dichloromethane
  9. dry with materialthe extract dried (MgSO4)
  10. filtrationfiltered
  11. washthe pad washed with dichloromethane
  12. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-21fbe1d54a3f40d9b500f6a7cba9daec
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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