Benzyl mercaptan → Benzyl (2-chloroprop-2-en-1-yl)carbamodithioate

HRID 841049Notes

Reaction equation

HRID 841049 reaction equation
[Cl:1][C:2](=[CH2:7])[CH2:3][N:4]=[C:5]=[S:6].[CH2:8]([SH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N12CCN(CC1)CC2>C(#N)C.C1(C)C=CC=CC=1>[CH2:8]([S:15][C:5](=[S:6])[NH:4][CH2:3][C:2]([Cl:1])=[CH2:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 9237DabcoHCID 26575Isothiocyanic acid, 2-chloroallyl ester

Product 1

HCID 54395229Benzyl (2-chloroprop-2-en-1-yl)carbamodithioate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

47 g of 2-chloro-allyl isothiocyanate and 40 g of benzyl mercaptan are dissolved in 150 ml of acetonitrile and 150 ml of toluene. Then 1 g of 1,4-diazabicyclo[2.2.2]octane is added and the mixture is heated to 75° C. and stirred for one hour. After cooling to room temperature, the solvent is removed by evaporation and the residue is crystallised from ether/hexane. In that manner the title product having a melting point of 46-48° C. (compound A) is obtained.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent is removed by evaporation
  3. customthe residue is crystallised from ether/hexane
  4. customis obtained

Sources & evidence

ORD record
ord-565f150157344df88599d00a9068ac64
Source dataset
uspto-grants-2002_04
Patent number
US06369233B1

Reaction notes

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