Methyl Isocyanate → 1,3-Dimethyl-3-(5-benzylthio-1,3,4-thiadiazol-2-yl)urea

HRID 1391192Notes

Reaction equation

HRID 1391192 reaction equation
[CH3:1][NH:2][C:3]1[S:4][C:5]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][N:7]=1.[CH3:16][N:17]=[C:18]=[O:19]>C(OCC)(=O)C>[CH3:16][NH:17][C:18]([N:2]([CH3:1])[C:3]1[S:4][C:5]([S:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:6][N:7]=1)=[O:19]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 8051175-(benzylthio)-N-methyl-1,3,4-thiadiazol-2-amine

Product 1

HCID 233476281,3-Dimethyl-3-(5-benzylthio-1,3,4-thiadiazol-2-yl)urea

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-methylamino-5-benzylthio-1,3,4-thiadiazole (4.0 g) in ethyl acetate (100 ml) was added 1.5 g of methyl isocyanate. The reaction was stirred at room temperature for 2 hrs. then heated at reflux for an additional 2 hrs. The product, 1,3-dimethyl-3-(5-benzylthio-1,3,4-thiadiazol-2-yl)urea, crystallized upon the addition of petroleum ether, was collected, washed with ether and dried to give 4.7 g, MP 139°-142° C.

Workup

  1. temperaturethen heated
  2. temperatureat reflux for an additional 2 hrs
  3. customThe product, 1,3-dimethyl-3-(5-benzylthio-1,3,4-thiadiazol-2-yl)urea, crystallized upon the addition of petroleum ether
  4. customwas collected
  5. washwashed with ether
  6. customdried
  7. customto give 4.7 g, MP 139°-142° C.

Sources & evidence

ORD record
ord-9f2c0ae4a1c94d62b5cc1ecf1e3d3ef3
Source dataset
uspto-grants-1979_02
Patent number
US04141717

Reaction notes

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