Methanol → HCID 46889870, compound

HRID 1927313Notes

Reaction equation

HRID 1927313 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-1353c321708d4535ad25a56d8f46faff
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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