Methanol → HCID 46889870, compound

HRID 244965Notes

Reaction equation

HRID 244965 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]([CH3:20])([CH3:19])[C:17](=N)[N:16]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([C:30]([F:33])([F:32])[F:31])[CH:23]=3)[C:15]2=[S:34])=[CH:10][CH:9]=1)(C)(C)C.C[OH:37].O>Cl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]([CH3:20])([CH3:19])[C:17](=[O:37])[N:16]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([C:30]([F:31])([F:33])[F:32])[CH:23]=3)[C:15]2=[S:34])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 86609852HCID 86609852, compound

Product 1

HCID 46889870HCID 46889870, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The mixture of 2c (0.15 g, 0.3 mmol) in HCl aq, 3N. (1 ml) and methanol (4 ml) was heated to reflux for 2 h. After being cooled to room temperature, the reaction mixture was poured into cold water (5 ml) and extracted with dichloromethane (8 ml). The organic layer was dried over MgSO4, concentrated and chromatographed (dichloromethane/acetone, 9:1) to yield 4-[3-(4-aminophenyl)-4,4-dimethyl-5-oxo-2-thioxoimidazolidin-1-yl]-2-trifluoromethylbenzonitrile, 2d, [RD9] (0.118 g, 0.29 mmol, 97%) as a yellow solid.

Workup

  1. temperatureto reflux for 2 h
  2. extractionextracted with dichloromethane (8 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed (dichloromethane/acetone, 9:1)

Sources & evidence

ORD record
ord-0151a6ea899c4284a6d72ec4b48f6b5a
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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