Methanol → 10,11-Dihydrodibenzo(b,f)(1,4)thiazepine

HRID 1598671Notes

Reaction equation

HRID 1598671 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.B.CSC.CO>O1CCCC1>[CH:9]1[C:8]2[CH2:2][NH:3][C:4]3[CH:16]=[CH:15][CH:14]=[CH:13][C:5]=3[S:6][C:7]=2[CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 374829DibenzothiazepinoneHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 1231048210,11-Dihydrodibenzo(b,f)(1,4)thiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 3.3 g of 10,11-dihydro-11-oxodibenz[b,f][1,4]thiazepine in 25 ml of tetrahydrofuran is added 4.0 ml of 10 molar borane-dimethylsulfide in tetrahydrofuran. The mixture is stirred[at room temperature for 18 hours, 50 ml of anhydrous methanol added and the solvent removed. An additional 30 ml of methanol is added and the solvent removed to give white crystals. A sample is purified by chromatography on silica gel with hexane-chloroform-ethyl acetate (2:1:1) as solvent to give white crystals, m.p. 145°-148° C.

Workup

  1. customthe solvent removed
  2. additionAn additional 30 ml of methanol is added
  3. customthe solvent removed
  4. customto give white crystals
  5. customA sample is purified by chromatography on silica gel with hexane-chloroform-ethyl acetate (2:1:1) as solvent
  6. customto give white crystals, m.p. 145°-148° C.

Sources & evidence

ORD record
ord-f27178c591ae4a8c83f04442ff60cda8
Source dataset
uspto-grants-1998_04
Patent number
US05739128

Reaction notes

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