Cyclohexanol → HCID 53693398, compound

HRID 329197Notes

Reaction equation

HRID 329197 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[S:8])=[O:5])[CH3:2].[CH:9]1([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C>O1CCCC1>[C:4]([NH:6][C:7](=[S:8])[O:15][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)([O:3][CH2:1][CH3:2])=[O:5]

Participants

5

Reactant 3

HCID 7966CyclohexanolHCID 8471TriethylamineHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 53693398HCID 53693398, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

65.6 g of ethoxycarbonyl isothiocyanate were added to a mixture of 50.1 g of cyclohexanol, 100 ml of tetrahydrofuran and 10 ml of triethylamine and the mixture was refluxed for 20 hours after which the tetrahydrofuran was distilled under reduced pressure. Ether was added to the residue and the ether phase was extracted with aqueous potassium hydroxide solutions. The aqueous phase was recovered by decanting and was acidified with N hydrochloric acid. The aqueous phase was extracted with ether and the ether phase was dried and concentrated to dryness under reduced pressure to obtain 82 g of cyclohexyl N-carbethoxy-thiocarbamate. The product was purified by chromatography over silica gel with elution with an 8-2 cyclohexane-ethyl acetate mixture.

Workup

  1. distillationwas distilled under reduced pressure
  2. additionEther was added to the residue
  3. extractionthe ether phase was extracted with aqueous potassium hydroxide solutions
  4. customThe aqueous phase was recovered
  5. customby decanting
  6. extractionThe aqueous phase was extracted with ether
  7. dry with materialthe ether phase was dried
  8. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-6053269d0759479abc75c5a50bbddb1e
Source dataset
uspto-grants-1977_04
Patent number
US04020076

Reaction notes

Loading…