(Dimethyl sulfide)trihydroboron → HCID 6918570, compound

HRID 1057639Notes

Reaction equation

HRID 1057639 reaction equation
B.CSC.[CH2:5]([N:12]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([O:25][CH2:26][CH2:27][NH:28][CH:29]=O)[C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[C:16]([CH3:31])[CH:17]=2)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C1COCC1>[CH2:5]([N:12]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([O:25][CH2:26][CH2:27][NH:28][CH3:29])[C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[C:16]([CH3:31])[CH:17]=2)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 86758821HCID 86758821, compound

Product 1

HCID 6918570HCID 6918570, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulfide (0.12 mL, 0.0013 mol) is added to a mixture of 2-[(9-benzyl-6-methyl-9H-carbazol-4-yl)oxy]ethylformamide (0.1565 g, 0.0013 mol) in dry THF (3 mL) and the mixture is stirred overnight at room temperature. The excess borane is cautiously quenched with methanol and the mixture is concentrated under reduced pressure. Methanol and dichloromethane are added to the residue and the solution is again concentrated under reduced pressure (repeated twice). The solids are then dissolved in methanol/dichloromethane and conc. HCl (27 drops) is added. After the mixture had stirred for 1.3 h, the solvent is removed under reduced pressure and the residue is partitioned between dichloromethane and aq. sodium bicarbonate. The combined organic layers are dried over sodium sulfate and concentrated to an oil. The oil is chromatographed on silica gel (40 mL) using acetone/dichloromethane/0.25% NH4OH (10/90, 20/80 and 50/50) to give 0.1300 g (86%) of the title compound; mp 96-96.75° C.; MS (ESI+) for C23H24N2O m/z 345.2 (M+H)+; IR (drift) 1600, 1580, 1467, 1449, 1341, 1307, 1268, 1242, 1151, 1128, 794, 779, 744, 718, 708 cm−1; 1H NMR (CDCl3) δ2.54, 2.61, 3.22, 4.39, 5.48, 6.68, 6.96, 7.11, 7.24, 7.31, 8.09. Anal. Calcd for C23H24N2O: C, 80.20; H, 7.02; N, 8.13. Found: C, 79.88; H, 7.15; N, 8.12.

Workup

  1. customThe excess borane is cautiously quenched with methanol
  2. concentrationthe mixture is concentrated under reduced pressure
  3. additionMethanol and dichloromethane are added to the residue
  4. concentrationthe solution is again concentrated under reduced pressure (
  5. dissolutionThe solids are then dissolved in methanol/dichloromethane
  6. additionconc. HCl (27 drops) is added
  7. stirringAfter the mixture had stirred for 1.3 h
  8. customthe solvent is removed under reduced pressure
  9. customthe residue is partitioned between dichloromethane and aq. sodium bicarbonate
  10. dry with materialThe combined organic layers are dried over sodium sulfate
  11. concentrationconcentrated to an oil
  12. customThe oil is chromatographed on silica gel (40 mL)

Sources & evidence

ORD record
ord-9b2f4c659bf440ada08328b21973edb4
Source dataset
uspto-grants-2003_02
Patent number
US06514968B1

Reaction notes

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