4-(Trifluoromethyl)aniline → N-(2,6-bis(trifluoromethyl)-4-pyridinyl)-N'-(4-trifluoromethylphenyl)thiourea

HRID 1065753Notes

Reaction equation

HRID 1065753 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[N:12]([C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[N:18]=[C:17]([C:25]([F:28])([F:27])[F:26])[CH:16]=1)=[C:13]=[S:14]>C1C=CC=CC=1.C(N(CC)CC)C>[F:27][C:25]([F:26])([F:28])[C:17]1[CH:16]=[C:15]([NH:12][C:13]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:4][CH:3]=2)=[S:14])[CH:20]=[C:19]([C:21]([F:24])([F:22])[F:23])[N:18]=1

Participants

5

Reactant 2

HCID 99644-(Trifluoromethyl)anilineHCID 133736064-Isothiocyanato-2,6-bis(trifluoromethyl)pyridine

Product 1

HCID 12945257N-(2,6-bis(trifluoromethyl)-4-pyridinyl)-N'-(4-trifluoromethylphenyl)thioureaYield 72.9%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 4-aminobenzotrifluoride (1.48 g) and 4-isothiocyanato-2,6-bis(trifluoromethyl)pyridine (2.5 g, 0.01 mole) in dry benzene (25 ml) containing several drops of triethylamine was heated under reflux for 7 hours. Removal of the solvent and triethylamine gave the title compound as a colorless solid 2.9 g, m.p. 125°-132° C. Crystallization from benzene furnished a sample, m.p. 132° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. customRemoval of the solvent and triethylamine

Sources & evidence

ORD record
ord-a9778566bd43446ea18099feab076bc7
Source dataset
uspto-grants-1982_05
Patent number
US04331669

Reaction notes

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