Ammonia → HCID 13289681, compound

HRID 1903717Notes

Reaction equation

HRID 1903717 reaction equation
[SH:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:4][N:3]=1.N.[F:23][C:24](I)([F:26])[F:25]>O1CCCC1>[F:23][C:24]([F:26])([F:25])[S:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:5]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 16843TrifluoroiodomethaneHCID 178505526HCID 178505526, compound

Product 1

HCID 13289681HCID 13289681, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Mercapto-4,5-bis(4-fluorophenyl)pyrimidine (5.04 g) was placed in a flask into which was condensed ~125 ml liquid ammonia. The resultant slurry was diluted with 30 ml tetrahydrofuran and cooled to -78°. Trifluoromethyl iodide (1.9 ml) was introduced as a gas and the cold bath was then removed. The reaction mixture was irradiated with a General Electric 275 W sun lamp for 2 hours. The ammonia was allowed to evaporate and the tetrahydrofuran removed in vacuo. The residue was dissolved in methylene chloride, washed with water and brine, dried and concentrated on the rotary evaporator. Crystallization from ethanol gave the title compound (2.1 g), m.p. 80°-83°. Infrared and H-NMR were consistent with the assigned structure. MS 368 (M+).

Workup

  1. temperaturecooled to -78°
  2. customthe cold bath was then removed
  3. customThe reaction mixture was irradiated with a General Electric 275 W sun lamp for 2 hours
  4. customto evaporate
  5. customthe tetrahydrofuran removed in vacuo
  6. dissolutionThe residue was dissolved in methylene chloride
  7. washwashed with water and brine
  8. customdried
  9. concentrationconcentrated on the rotary evaporator
  10. customCrystallization from ethanol

Sources & evidence

ORD record
ord-fc273bdeee7c4a6b9bae3d2107b6a524
Source dataset
uspto-grants-1984_03
Patent number
US04438117

Reaction notes

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