Ethyl isothiocyanatoformate → HCID 86606225, compound

HRID 908195Notes

Reaction equation

HRID 908195 reaction equation
C(OC([N:6]=[C:7]=[S:8])=O)C.[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[S:20][C:19]([NH2:21])=[N:18][N:17]=2)[CH2:12][CH2:11]1>C(#N)C.CN(C=O)C>[CH3:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[S:20][C:19]([NH:21][C:7]([NH2:6])=[S:8])=[N:18][N:17]=2)[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 15000235-(4-Methyl-1-piperazinyl)-1,3,4-thiadiazol-2-amine

Product 1

HCID 86606225HCID 86606225, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Ethoxycarbonylisothiocyanate (0.346 ml, 2.96 mmol) is added dropwise to a stirred suspension of 5-(4-Methyl-piperazin-1-yl)-[1,3,4]thiadiazol-2-ylamine (63b) (0.59 g, 2.96 mmol) in acetonitrile (15 ml) and DMF (5 ml). The reaction is heated at 80° C. for 7 h followed by removal of the solvent. The residue heated in 2M aqueous NaOH (80 ml) at reflux for 30 minutes. After cooling to room temperature the solution is neutralised by addition of 6M aqueous HCl and the titled product is removed by filtration and dried under vacuum.

Workup

  1. customfollowed by removal of the solvent
  2. temperatureThe residue heated in 2M aqueous NaOH (80 ml)
  3. temperatureat reflux for 30 minutes
  4. temperatureAfter cooling to room temperature the solution
  5. additionis neutralised by addition of 6M aqueous HCl
  6. customthe titled product is removed by filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-660ed6a618424f439c05519093e33d57
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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