Ethyl isothiocyanatoformate → Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate

HRID 1099100Notes

Reaction equation

HRID 1099100 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH3:10])=[CH:4][N:3]=1.[CH3:11][CH2:12][O:13][C:14]([N:16]=[C:17]=[S:18])=[O:15]>C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:17]([NH:16][C:14](=[O:15])[O:13][CH2:12][CH3:11])=[S:18])[C:5]([O:9][CH3:10])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 85320Ethyl isothiocyanatoformateHCID 569495382-Chloro-5-methoxypyrimidin-4-amine

Product 1

HCID 56949522Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

2-Chloro-5-methoxypyrimidin-4-amine (1) (6.4 g, 0.040 mol) was suspended in ethyl acetate (100 mL) and heated to near reflux. Ethyl isothiocyanatidocarbonate (8.9 g, 1.7 eq) was added all at once, and the mixture was maintained at reflux for 10 hours. The resulting slurry was cooled to 15° C., and the solid product was isolated by filtration and the cake washed with fresh ethyl acetate to afford the title compound in several crops as a solid (7.8 g, 67%): mp 182° C.; 1H NMR (DMSO-d6): δ 11.97 (s, 1H), 11.72 (s, 1H), 8.50 (s, 1H), 4.22 (q, 2H), 3.72 (s, 3H), 1.17 (t, 3H); 13C NMR (DMSO-d6): δ 177.82, 153.58, 150.00, 149.01, 144.26, 142.63, 62.76, 57.56, 14.44; Mass spec (accurate mass): Calcd for C9H11ClN4O3S: 290.024039; found, 290.0241.

Workup

  1. temperatureheated
  2. temperatureto near reflux
  3. temperaturewas maintained
  4. temperatureat reflux for 10 hours
  5. customthe solid product was isolated by filtration
  6. washthe cake washed with fresh ethyl acetate

Sources & evidence

ORD record
ord-b49d38916fc2436091bf798f91c3fa5e
Source dataset
uspto-grants-2012_03
Patent number
US08143395B2

Reaction notes

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