Dimethylamine → Cyclohexanamine, N-cyclohexyl-N-[[(dimethylamino)thioxomethyl]thio]-

HRID 435834Notes

Reaction equation

HRID 435834 reaction equation
[CH3:1][NH:2][CH3:3].[CH:4]1([NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[O-]Cl.[Na+].C([O-])(O)=O.[Na+].C([O-])([O-])=O.[Na+].[Na+].[C:31](=[S:33])=[S:32]>O.C(Cl)(Cl)(Cl)Cl>[CH3:1][N:2]([C:31]([S:33][N:10]([CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1)[CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)=[S:32])[CH3:3]

Participants

9

Reactant 6

HCID 674DimethylamineHCID 6348Carbon DisulfideHCID 7582DicyclohexylamineHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 23665760Sodium Hypochlorite

Product 1

HCID 104035Cyclohexanamine, N-cyclohexyl-N-[[(dimethylamino)thioxomethyl]thio]-

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
10 °C

Procedure

N,N-dimethylthiocarbamyl-N',N'-dicyclohexylsulfenamide was prepared. 100 milliliters of carbon tetrachloride, 39.6 grams of a solution of dimethylamine at 25% by weight in water (0.22 mole) and 36.2 grams (0.2 mole) of dicyclohexylamine were placed in a reactor vessel and the mixture cooled to 10° C. 114 milliliters of a solution of NaOCl at 14% by weight in water (0.23 mole) was added and the mixture stirred for 15 minutes at 10° to 15° C. 200 milliliters of water containing 25 grams of NaHCO3 and 11 grams of Na2CO3 was then added as a buffer solution. The mixture was warmed to 20° C. and 15.2 grams (0.2 mole) of carbon disulfide was added while stirring. The mix was stirred for 40 minutes at a temperature of about 32°-35° C. The mixture was allowed to settle and the non-aqueous phase separated out and filtered. The carbon tetrachloride was then evaporated off, leaving 61 grams of a thick liquid. 150 milliliters of methanol was added and the liquid first dissolved, then a solid precipitated out. The methanol slurry was cooled to -10° C. and filtered. The solids isolated were dried, and 44.1 grams of a white crystalline solid having a melting point of 85°-87° C. was obtained. The yield was 77% by weight based upon the weight of carbon disulfide used. The N,N-dimethylthiocarbamyl-N',N'-dicyclohexylsulfenamide was identified by its Infra-red spectrum. The calculated element weights for the formula C15H28N2S2 were 9.32% nitrogen, 60.0% carbon, and 9.32% hydrogen. Analytical values were 9.34% nitrogen, 59.8% carbon, and 9.60% hydrogen respectively.

Workup

  1. temperatureThe mixture was warmed to 20° C.
  2. stirringwhile stirring
  3. stirringThe mix was stirred for 40 minutes at a temperature of about 32°-35° C
  4. customthe non-aqueous phase separated out
  5. filtrationfiltered
  6. customThe carbon tetrachloride was then evaporated off

Sources & evidence

ORD record
ord-564f894ab56b432690d36a2f9e8c4cad
Source dataset
uspto-grants-1977_02
Patent number
US04006251

Reaction notes

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