Hydrochloric Acid → HCID 57842645, compound

HRID 735526Notes

Reaction equation

HRID 735526 reaction equation
B.[NH2:2][C:3]1[CH:4]=[CH:5][C:6]([S:13][CH:14]([CH3:16])[CH3:15])=[C:7]([CH:12]=1)[C:8]([NH:10][CH3:11])=O.Cl>C1COCC1>[CH:14]([S:13][C:6]1[CH:5]=[CH:4][C:3]([NH2:2])=[CH:12][C:7]=1[CH2:8][NH:10][CH3:11])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 578428575-Amino-2-(isopropylthio)-N-methylbenzamide

Product 1

HCID 57842645HCID 57842645, compoundYield 112.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Borane (1M solution in THF, 10 mL, 10 mmol) was added slowly dropwise to a solution of 16C (0.98 g, 4.37 mmol) in THF (60 mL) at 0° C. The reaction mixture was then heated to 70° C. overnight. The reaction mixture was cooled in an ice bath and quenched by cautious addition of hydrochloric acid (2N, 12 mL, 24 mmol). The reaction mixture was refluxed for 2 h and then concentrated almost to dryness in vacuo. The residue was coevaporated with methanol (3×), diluted with ethyl acetate and sodium hydroxide solution (2N). The aqueous layer was extracted with ethyl acetate (3×), dried (MgSO4), and concentrated in vacuo to give 16D (1.03 g, 100%) as a clear oil. MS (ESI) m/z 211.1 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. temperatureThe reaction mixture was refluxed for 2 h
  3. concentrationconcentrated almost to dryness in vacuo
  4. additiondiluted with ethyl acetate and sodium hydroxide solution (2N)
  5. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0bc457f932ae4f8b8c5c62b90543ee30
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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