Ethyl isothiocyanatoformate → HCID 57476592, compound

HRID 1875971Notes

Reaction equation

HRID 1875971 reaction equation
[CH2:1]([O:3][C:4]([N:6]=[C:7]=[S:8])=[O:5])[CH3:2].[Cl:9][C:10]1[N:15]=[C:14](Cl)[C:13]([NH2:17])=[CH:12][N:11]=1>CO>[Cl:9][C:10]1[N:11]=[CH:12][C:13]2[N:17]=[C:7]([NH:6][C:4](=[O:5])[O:3][CH2:1][CH3:2])[S:8][C:14]=2[N:15]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 2577975-Amino-2,4-dichloropyrimidine

Product 1

HCID 57476592HCID 57476592, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethoxycarbonyl isothiocyanate (4.32 mL, 36.6 mmol) and 2,4-dichloro-pyrimidin-5-ylamine (3.00 g, 18.29 mmol) were mixed neat and sonicated for 5 minutes to help dissolve. The mixture was stirred at ambient temperature for 10 minutes, at which time the entire mixture had solidified. Methanol (100 mL) was added and the mixture was refluxed for 30 minutes, cooled to ambient temperature and the solids were collected by filtration to afford ethyl 5-chlorothiazolo[5,4-d]pyrimidin-2-ylcarbamate (3.8 g, 80% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.64 (s, 1H) 9.05 (s, 1H) 4.31 (q, J=7.19 Hz, 2H) 1.32 (t, J=7.15 Hz, 3H).

Workup

  1. customsonicated for 5 minutes
  2. dissolutionto help dissolve
  3. temperaturethe mixture was refluxed for 30 minutes
  4. temperaturecooled to ambient temperature
  5. filtrationthe solids were collected by filtration

Sources & evidence

ORD record
ord-97a8884217814f86add29c88f61e6025
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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