Carbon Disulfide → 1-Isothiocyanato-1,2,3,4-tetrahydronaphthalene

HRID 1606704

Reaction equation

HRID 1606704 reaction equation
[CH:1]1([NH2:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:19](=S)=[S:20].C1(N=C=NC2CCCCC2)CCCCC1>C(OCC)(=O)C>[CH:1]1([N:11]=[C:19]=[S:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 180661,2,3,4-Tetrahydro-1-naphthylamine

Product 1

HCID 213934781-Isothiocyanato-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 0.01 mole of 1,2,3,4-tetrahydro-1-naphthylamine in ethyl acetate is added 0.01 mole of triethylamine and 0.011 mole of carbon disulfide. The mixture is stirred about one hour and then 0.01 mole of dicyclohexyl carbodiimide is added. The mixture is stirred overnight, and the mixture filtered to remove solid dicyclohexylthiourea. The filtrate is evaporated, and the residue is purified by dry column chromatography to give 1,2,3,4-tetrahydro-1-naphthyl isothiocyanate.

Workup

  1. stirringThe mixture is stirred overnight
  2. filtrationthe mixture filtered
  3. customto remove solid dicyclohexylthiourea
  4. customThe filtrate is evaporated
  5. customthe residue is purified
  6. customby dry column chromatography

Sources & evidence

ORD record
ord-9333fce444804ddba252135245397d90
Source dataset
uspto-grants-1976_04
Patent number
US03953506

Linked notes

Loading…