2-Aminothiazole → Thiourea, N-(3-phenylpropyl)-N'-2-thiazolyl-

HRID 861574Notes

Reaction equation

HRID 861574 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]=[C:11]=[S:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1.C(OCC)(=O)C>CN(C)C=O>[C:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)=[S:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 8857Ethyl AcetateHCID 758153-Phenylpropyl isothiocynate

Product 1

HCID 3001100Thiourea, N-(3-phenylpropyl)-N'-2-thiazolyl-Yield 16.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-phenylpropyl isothiocyanate (500 mg, 2.82 mmol) and 2-aminothiazole (300 mg, 3.0 mmol) in N,N-dimethylformamide (10 mL) was heated to 100° C. After 20 h, the reaction was cooled to room temperature and poured into ethyl acetate. The organic phase was washed with 1N hydrochloric acid, water (3×), and brine. The organic layer was dried over sodium sulfate, filtered and concentrated. The solid obtained was purified by flash chromatography on silica gel (1% ethyl acetate in dichloromethane) and then recrystallized from ethyl acetate to provide 129 mg of the title product. A second crop was recrystallized from 1:1 ethyl acetate/hexanes to provide another 110 mg of the title product. Total yield of the title product: 239 mg (30%) as an off-white solid. A sample was recrystallized again from ethyl acetate:

Workup

  1. washThe organic phase was washed with 1N hydrochloric acid, water (3×), and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe solid obtained
  6. customwas purified by flash chromatography on silica gel (1% ethyl acetate in dichloromethane)
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e3b61f3c34ac4ff193fad7ffa02d75ff
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Reaction notes

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