Water → HCID 56949576, compound

HRID 1099101Notes

Reaction equation

HRID 1099101 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([NH:11]C(=O)OCC)=S)[C:5]([O:17][CH3:18])=[CH:4][N:3]=1.Cl.[NH2:20]O.C(=O)(O)[O-].[Na+].O>C(=O)([O-])[O-].[Na+].[Na+].C(#N)C>[Cl:1][C:2]1[N:7]2[N:11]=[C:9]([NH2:20])[N:8]=[C:6]2[C:5]([O:17][CH3:18])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 56949522Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate

Product 1

HCID 56949576HCID 56949576, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateCatalystHCID 6342AcetonitrileSolvent

Procedure

Ethyl [(2-chloro-5-methoxypyrimidin-4-yl)amino]carbonothioylcarbamate (2) (290 mg, 1.0 mmol), hydroxylamine hydrochloride (143 mg, 2 eq), and sodium bicarbonate (170 mg, 2 eq) were combined. Water (5 mL) and acetonitrile (5 mL) were added at room temperature. The resulting slurry was stirred at room temperature overnight, then treated with 20 drops of saturated aqueous sodium carbonate solution. The resulting solution was sparged with nitrogen and cooled, producing the product as a chalky precipitate, which was collected by filtration (in two crops), washed with water, and dried to obtain the title compound as a solid (139 mg, 68%): mp 251° C.; 1H NMR (DMSO-d6) δ 7.73 (s, 1H), 3.98 (s 3H); 6.63 (s, 2H); 13C NMR (DMSO-d6): 166.30, 148.14, 128.91, 124.67, 57.51; Mass spec (accurate mass): Calcd for C6H6ClN5O 199.026087; found, 199.0256.

Workup

  1. customThe resulting solution was sparged with nitrogen
  2. temperaturecooled
  3. customproducing the product as a chalky precipitate, which
  4. filtrationwas collected by filtration (in two crops)
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-4b0d709f73a241a9b8afc4f11907afef
Source dataset
uspto-grants-2012_03
Patent number
US08143395B2

Reaction notes

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