Methyl isothiocyanate → HCID 86744904, compound

HRID 1086501Notes

Reaction equation

HRID 1086501 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH2:7])[N:4]([CH3:8])[C:3]1=[S:9].CNCC#N.CN=C=S.[CH3:19][N:20]=[C:21]=[O:22]>N1C=CC=CC=1>[CH3:1][N:2]1[CH2:6][CH:5]([NH:7][C:21]([NH:20][CH3:19])=[O:22])[N:4]([CH3:8])[C:3]1=[S:9]

Participants

6

Reactant 4

HCID 11167Methyl isothiocyanateHCID 12228Methyl IsocyanateHCID 36652Acetonitrile, 2-(methylamino)-HCID 12571560HCID 12571560, compound

Product 1

HCID 86744904HCID 86744904, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3.22 grams (0.0225 mol) of 1,3-dimethyl-4-amino-4-imidazoline-2-thione (prepared from methylaminoacetonitrile and methyl isothiocyanate by the method of T. Kinoshita et al, Bull. Chem. Soc. Japan., 53, 442 (1980)) in 12 mL of pyridine under an atmosphere of nitrogen was added with stirring 2.61 grams (0.0457 mol) of methyl isocyanate. The mixture became exothermic. Stirring was continued overnight whereupon a solid precipitate formed in the reaction mixture. The latter was collected by filtration and washed with isopropyl alcohol to obtain 2.11 grams of 1,3-dimethyl-4-(methylaminocarbonylamino)-imidazoline-2-thione, m.p. 200°-201° C.

Workup

  1. customformed in the reaction mixture
  2. filtrationThe latter was collected by filtration
  3. washwashed with isopropyl alcohol

Sources & evidence

ORD record
ord-e9e24ae8412a4c0fadeb00d9d7e36249
Source dataset
uspto-grants-1991_07
Patent number
US05030644

Reaction notes

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