1,2-Cyclohexanediol → 4,5,6,7-Tetrahydrobenzimidazol-2-thione

HRID 486087

Reaction equation

HRID 486087 reaction equation
O[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1O.[NH2:9][C:10]([NH2:12])=[S:11]>C(O)CCCCC>[N:9]1[C:10](=[S:11])[N:12]=[C:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]=12

Participants

4

Reactant 2

HCID 136011,2-CyclohexanediolHCID 2723790Thiourea

Product 1

HCID 190975414,5,6,7-Tetrahydrobenzimidazol-2-thioneYield 19.5%

Reagents, catalysts & solvents 1

HCID 81031-HexanolSolvent

Procedure

Part A. A solution of 2-hydroxycyclohexanol (2.28 g, 0.02 mol), thiourea (1.52 g, 0.02 mol) and hexanol (30 ml), equipped with a column of 4Å sieves and a condenser, was heated to 160° for five hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature and was concentrated in vacuo to give a solid. The solid was triturated with ethyl ether (3×50 ml) to give 4,5,6,7-tetrahydrobenzimidazol-2-thione (0.6 g, 0.0039 mol) which was not purified but was taken on to the next step as a crude solid.

Workup

  1. temperaturewas heated to 160° for five hours under a nitrogen atmosphere
  2. concentrationwas concentrated in vacuo
  3. customto give a solid
  4. customThe solid was triturated with ethyl ether (3×50 ml)

Sources & evidence

ORD record
ord-915fe78de93f4d13a1825becaa68dcc1
Source dataset
uspto-grants-1994_03
Patent number
US05290801

Linked notes

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