6-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione → HCID 12297296, compound

HRID 2036281Notes

Reaction equation

HRID 2036281 reaction equation
O.[SH-:2].[Na+].Cl[C:5]1[N:10]([CH3:11])[C:9](=[O:12])[N:8]([CH3:13])[C:7](=[O:14])[CH:6]=1>O.C(Cl)(Cl)Cl.C(O)C>[SH:2][C:5]1[N:10]([CH3:11])[C:9](=[O:12])[N:8]([CH3:13])[C:7](=[O:14])[CH:6]=1

Participants

6

Reactant 2

HCID 814426-Chloro-1,3-dimethyl-2,4(1H,3H)-pyrimidinedioneHCID 16211346Sodium hydrosulfide hydrate

Product 1

HCID 12297296HCID 12297296, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

A solution of sodium hydrosulphide hydrate (74.77 g, 1335.243 mmol) in water (125 ml) was added dropwise to a stirred solution of Step 1 (50.0 g, 286.532 mmol) in chloroform (250 ml) and ethanol (636 ml) in an ice water bath, and the mixture was stirred at room temperature overnight. The reaction mixture was evaporated to dryness in vacuo at room temperature. The residue obtained was dissolved in water (100 ml) and extracted with dichloromethane (2×100 ml). The aqueous layer was acidified with 1 N HCl. Precipitated solid was filtered, washed with water (2×100 ml) and dried to obtain 49.22 g of the product as a pale yellow solid; 1H NMR (300 MHz, CDCl3) δ 3.33 (s, 3H), 3.74 (s, 3H), 4.17 (s, 2H).

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo at room temperature
  2. customThe residue obtained
  3. extractionextracted with dichloromethane (2×100 ml)
  4. customPrecipitated solid
  5. filtrationwas filtered
  6. washwashed with water (2×100 ml)
  7. customdried

Sources & evidence

ORD record
ord-173a7186d25248459b01acabd665e662
Source dataset
uspto-grants-2013_11
Patent number
US08575178B2

Reaction notes

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