Methanol → HCID 59828901, compound

HRID 1191061Notes

Reaction equation

HRID 1191061 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]([S:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)=[O:4].B.CSC.CO.[H][H]>C1COCC1>[CH3:1][N:2]([CH3:14])[C:3]([S:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 5516014-dimethylcarbamoylthio-benzonitrileHCID 12423031(Dimethyl sulfide)trihydroboronHCID 178418361HCID 178418361, compound

Product 1

HCID 59828901HCID 59828901, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 4-dimethylcarbamoylthio-benzonitrile (3.07 g, 14.9 mmol) in anhydrous THF (30 mL). Add borane-dimethylsulfide complex (4.24 mL, 44.7 mmol, 1M solution in diethyl ether) and stir the mixture at room temperature for 3 h. Add methanol dropwise until hydrogen evolution ceases. Concentrate the mixture in vacuo and purify the crude mixture by SCX chromatography eluting with methanol and 2M ammonia in methanol to obtain the title compound as a slightly impure oil (2.9 g). Dissolve the oil (2.9 g) in DCM and add 2M hydrogen chloride in ether. Stir the mixture for 1 h and concentrate in vacuo to obtain a solid. Suspend the solid in DCM and add diethyl ether to precipitate the salt. Filter and dry the solid in vacuo to obtain the hydrochloride salt of the title compound as a white solid (2.33 g, 64%). Elute the compound through a SCX column to obtain the desired intermediate as an oil. MS (ES+) m/z: 211 (M+H)+.

Workup

  1. concentrationConcentrate the mixture in vacuo
  2. custompurify the crude mixture by SCX chromatography
  3. washeluting with methanol and 2M ammonia in methanol

Sources & evidence

ORD record
ord-ee40b95e32644154a0e130c1790950db
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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