Ethyl isothiocyanatoformate → 3-(5-Thioureido-[1,3,4]thiadiazol-2-yl)-propionic acid

HRID 908188Notes

Reaction equation

HRID 908188 reaction equation
C(OC([N:6]=[C:7]=[S:8])=O)C.C[O:10][C:11](=[O:20])[CH2:12][CH2:13][C:14]1[S:15][C:16]([NH2:19])=[N:17][N:18]=1>ClCCl>[NH:19]([C:16]1[S:15][C:14]([CH2:13][CH2:12][C:11]([OH:10])=[O:20])=[N:18][N:17]=1)[C:7]([NH2:6])=[S:8]

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 54474128Methyl 3-(5-amino-1,3,4-thiadiazol-2-yl)propanoate

Product 1

HCID 866062213-(5-Thioureido-[1,3,4]thiadiazol-2-yl)-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethoxycarbonyl isothiocyanate (0.656 ml, 5.61 mmol) is added dropwise to a stirred suspension of 3-(5-amino-[1,3,4]thiadiazol-2-yl)-propionic acid methyl ester (56a) in dichloromethane (30 ml). The reaction is at room temperature for 18 hours. After removing the solvent, aqueous sodium hydroxide (2M, 10 ml) is added and the stirred mixture is heated at reflux for 3 hours. The solution is allowed to cool to room temperature and brought to pH 3 by the addition of 6M aqueous HCl. The titled compound which precipitates is removed by filtration, washed with ethyl acetate and dried in vacuo.

Workup

  1. customAfter removing the solvent, aqueous sodium hydroxide (2M, 10 ml)
  2. additionis added
  3. temperaturethe stirred mixture is heated
  4. temperatureat reflux for 3 hours
  5. additionbrought to pH 3 by the addition of 6M aqueous HCl
  6. customThe titled compound which precipitates
  7. customis removed by filtration
  8. washwashed with ethyl acetate
  9. customdried in vacuo

Sources & evidence

ORD record
ord-14756cade07a43f999de5723cf6e72a7
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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