1,1,1-Trifluoro-2-isothiocyanatoethane → 4-[3-(2,2,2-Trifluoroethyl)thioureido]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine

HRID 34770

Reaction equation

HRID 34770 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:9][CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[N:3]=1.[F:23][C:24]([F:30])([F:29])[CH2:25][N:26]=[C:27]=[S:28]>C(#N)C>[F:23][C:24]([F:30])([F:29])[CH2:25][NH:26][C:27](=[S:28])[NH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8][S:9][CH2:10][CH2:11][N:12]2[C:13](=[O:22])[C:14]3=[CH:21][CH:20]=[CH:19][CH:18]=[C:15]3[C:16]2=[O:17])[N:3]=1

Participants

4

Reactant 2

HCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 212988184-Amino-2-[(2-phthalimidoethyl)thiomethyl)pyrimidine

Product 1

HCID 538482754-[3-(2,2,2-Trifluoroethyl)thioureido]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidineYield 62.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-amino-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine (5.9 g.), 2,2,2-trifluoroethylisothiocyanate (3.9 g.) and acetonitrile (20 ml.) was stirred at 70° for 72 hours. The reaction mixture was cooled and the crystalline precipitate collected to give 4-[3-(2,2,2-trifluoroethyl)thioureido]-2-[(2-phthalimidoethyl)thiomethyl]pyrimidine (5.35 g.), m.p. 178°-179°.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe crystalline precipitate collected

Sources & evidence

ORD record
ord-1167a016d84a432a991c34ad0be5e4e8
Source dataset
uspto-grants-1988_08
Patent number
US04762932

Linked notes

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