Ethyl isothiocyanatoformate → HCID 57476592, compound

HRID 250106Notes

Reaction equation

HRID 250106 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, 1 H) 9.05 (s, 1 H) 4.31 (q, J=7.19 Hz, 2 H) 1.32 (t, J=7.15 Hz, 3 H).

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-b577a63e1316425aa9a46f784363f765
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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