Hydrochloric Acid → N-(2,6-Diisopropyl-phenyl)-N'-(3-trifluoromethyl-cyclohexyl)thiourea

HRID 1701567

Reaction equation

HRID 1701567 reaction equation
[F:1][C:2]([F:11])([F:10])[CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH2:9])[CH2:4]1.[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[C:16]=1[N:24]=[C:25]=[S:26])([CH3:14])[CH3:13].Cl>>[CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:22])[CH3:23])[C:16]=1[NH:24][C:25]([NH:9][CH:5]1[CH2:6][CH2:7][CH2:8][CH:3]([C:2]([F:10])([F:11])[F:1])[CH2:4]1)=[S:26])([CH3:13])[CH3:14]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1411942-Isothiocyanato-1,3-bis(propan-2-yl)benzeneHCID 162277663-(Trifluoromethyl)cyclohexylamine (cis-and trans-mixture)

Product 1

HCID 20347045N-(2,6-Diisopropyl-phenyl)-N'-(3-trifluoromethyl-cyclohexyl)thiourea

Procedure

16.0 g of 3-trifluoromethyl-cyclohexylamine are taken and 18.0 g of 2,6-diisopropyl-phenyl isothiocyanate are introduced whilst stirring. The reaction commences with slight evolution of heat. The mixture is left to stand for 12 hours and is then stirred with dilute hydrochloric acid. The crystalline product is filtered off, triturated with dilute methanol, filtered off and dried. The compound is obtained in the form of a stereomer mixture of melting point 67°-75° C.; yield 27 g. The elementary analysis and NMR and IR spectra agree with the assumed structure.

Workup

  1. customThe reaction commences with slight evolution
  2. temperatureof heat
  3. waitThe mixture is left
  4. filtrationThe crystalline product is filtered off
  5. customtriturated with dilute methanol
  6. filtrationfiltered off
  7. customdried
  8. customThe compound is obtained in the form of a stereomer mixture of melting point 67°-75° C.

Sources & evidence

ORD record
ord-4ae2509c66324cd5a707c69dd2da05a1
Source dataset
uspto-grants-1980_03
Patent number
US04194008

Linked notes

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