Methanol → HCID 46889870, compound

HRID 2233664Notes

Reaction equation

HRID 2233664 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-b0649020ed2e4758b7e6dc0c38c291f7
Source dataset
uspto-grants-2010_05
Patent number
US07709517B2

Reaction notes

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