Carbon Disulfide → HCID 21563667, compound

HRID 1580683Notes

Reaction equation

HRID 1580683 reaction equation
C(N(CC)CC)C.[C:8](=[S:10])=S.[CH3:11][C:12]1[CH:28]=[CH:27][C:15]([O:16][C:17]2[S:18][C:19]3[CH:25]=[C:24]([NH2:26])[CH:23]=[CH:22][C:20]=3[N:21]=2)=[CH:14][CH:13]=1.P(Cl)(Cl)(Cl)=O>C(OCC)C>[CH3:11][C:12]1[CH:28]=[CH:27][C:15]([O:16][C:17]2[S:18][C:19]3[CH:25]=[C:24]([N:26]=[C:8]=[S:10])[CH:23]=[CH:22][C:20]=3[N:21]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 21563669HCID 21563669, compound

Product 1

HCID 21563667HCID 21563667, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Additions are made dropwise, at -10° to -5°, firstly of 31 ml of triethylamine and then of 4.3 ml of carbon disulphide to 18.4 g of 2-(4'-methylphenoxy)-6-aminobenzothiazole in 360 ml of absolute diethyl ether. Stirring is continued for ca. 12 hours at room temperature; the mixture is cooled to 0°, and an addition made at this temperature, within 30 minutes, of 6.7 ml of phosphorus oxychloride in 80 ml of absolute diethyl ether. After 10 hours' stirring at room temperature, filtration is performed; the filter residue is washed firstly with diethyl ether and then with water and dried. the product is afterwards chromatographed through aluminium oxide, with methylene chloride as the eluant, to obtain 2-(4'-methylphenoxy)-6-isothiocyanobenzothiazole, M.P. 121° - 123°.

Workup

  1. temperaturethe mixture is cooled to 0°
  2. additionan addition
  3. stirringAfter 10 hours' stirring at room temperature
  4. filtrationfiltration
  5. washthe filter residue is washed firstly with diethyl ether
  6. dry with materialwith water and dried
  7. customthe product is afterwards chromatographed through aluminium oxide, with methylene chloride as the eluant

Sources & evidence

ORD record
ord-d395758d8b9c4adaa258d794455c9739
Source dataset
uspto-grants-1976_01
Patent number
US03933841

Reaction notes

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