Cyclohexylamine → N-(1-adamantyl)-N'-cyclohexylthiourea

HRID 436001

Reaction equation

HRID 436001 reaction equation
[C:1]12([N:11]=[C:12]=[S:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.NC(N)=S>CCOCC>[C:1]12([NH:11][C:12]([NH:20][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[S:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 107279Adamantyl isothiocyanateHCID 2723790Thiourea

Product 1

HCID 4328819N-(1-adamantyl)-N'-cyclohexylthiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The thiourea is prepared by reacting 19.3 g. (0.1 mole) of 1-adamantyl isothiocyanate with 10 g. (0.1 mole) of cyclohexylamine in 250 ml. of ether at room temperature for 3 hrs. The thiourea which separates from solution is collected: 23.5 g., mp. 175-175.5. Evaporation of the ether filtrate to a small volume gives a second crop, 5.2 g., mp. 176-178. The combined yield is 28.7 g. (98.5 percent). A sample is recrystallized from alcohol and melts at 176°-177°.

Workup

  1. customis collected
  2. customEvaporation of the ether filtrate to a small volume
  3. customgives a second crop, 5.2 g
  4. customA sample is recrystallized from alcohol and melts at 176°-177°

Sources & evidence

ORD record
ord-f19c9dab45e24f08988a03c2f86f46fd
Source dataset
uspto-grants-1977_02
Patent number
US04007181

Linked notes

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