Ethanol → 2-Hydroxy-5-nitrothiocarbanilide

HRID 1658238Notes

Reaction equation

HRID 1658238 reaction equation
[C:1](=[S:3])=S.C(O)C.[NH2:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[NH2:14]>O>[NH:7]1[CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]2[NH:14][C:1]1=[S:3]

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 46101,2-DiaminocyclohexaneHCID 6348Carbon Disulfide

Product 1

HCID 28238482-Hydroxy-5-nitrothiocarbanilide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 67 g. of carbon disulfide in 300 ml. of ethanol is added dropwise with stirring a solution of 100 g. of 1,2-diaminocyclohexane in 100 ml. of ethanol. The resulting solution is stirred one-half hour after addition; liquid eliminated and the residue dissolved in 300 ml. of water and heated at reflux for 18 hours. The precipitate which forms on cooling is filtered off, washed with water and then with ether and dried under reduced pressure to obtain 3a,4,5,6,7,7a-hexahydro-2-benzimidazolin-thione, m.p. 170°C.

Workup

  1. additionTo a mixture of 67 g
  2. stirringThe resulting solution is stirred one-half hour
  3. additionafter addition
  4. dissolutionthe residue dissolved in 300 ml
  5. temperatureat reflux for 18 hours
  6. temperatureon cooling
  7. filtrationis filtered off
  8. washwashed with water
  9. dry with materialwith ether and dried under reduced pressure

Sources & evidence

ORD record
ord-725f456e7c124d14b2d6b200aa96d63c
Source dataset
uspto-grants-1976_06
Patent number
US03963720

Reaction notes

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