Hydrochloric Acid → HCID 58495504, compound

HRID 1191057Notes

Reaction equation

HRID 1191057 reaction equation
[CH:1]1([S:7]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.C1COCC1.Cl>C1COCC1>[CH:1]1([S:7]([C:10]2[CH:11]=[CH:12][C:13]([CH2:14][NH2:15])=[CH:16][CH:17]=2)(=[O:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 58495697HCID 58495697, compound

Product 1

HCID 58495504HCID 58495504, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve 4-cyclohexanesulfonyl-benzonitrile (1.27 g, 5.1 mmol) in anhydrous THF (15 mL) at 0° C. under nitrogen and then add a solution of borane-THF complex (15.3 mL, 15.3 mL, 1M solution in THF). Stir overnight while warming to room temperature. Add the reaction to a mixture of 5N aqueous HCl (50 mL), THF (50 mL) and ice and stir for 1 hour. Concentrate the mixture in vacuo and take up the resulting white residue through a SCX-2 column eluting with methanol followed by 3N ammonia in methanol to obtain the title compound as a white solid (625 mg, 50%). MS (ES+) m/z: 254.1 (M+H)+

Workup

  1. additionAdd
  2. customthe reaction
  3. stirringstir for 1 hour
  4. concentrationConcentrate the mixture in vacuo
  5. washeluting with methanol

Sources & evidence

ORD record
ord-7d250eb4f86d4ea0b6db3b1debc731cd
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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