Sodium Carbonate → HCID 18625224, compound

HRID 1859379Notes

Reaction equation

HRID 1859379 reaction equation
[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[C:6]1[S:7][CH:8]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:10]=1)[CH2:2][CH2:3][CH3:4].P(Cl)(Cl)(Cl)=O.[C:28](=O)([O-])[O-:29].[Na+].[Na+]>CN(C=O)C.O>[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[C:6]1[S:7][C:8]([CH:28]=[O:29])=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 18625226HCID 18625226, compound2×

Product 1

HCID 18625224HCID 18625224, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 100.8 g (316.5 mmol) of crude 2-di-n-butylamino-4-(3-methoxyphenyl)thiazole (compound 2-12) and 630 ml of DMF was added, over about 30 mins, a solution of 55.81 g (364 mmol) of phosphorus oxychloride in 188 ml of DMF. The mixture was stirred overnight and poured into a solution of 158.1 g of sodium carbonate in 3.5 l of water. The oily precipitate was extracted with methylene chloride, and the extract was washed with water, dried over magnesium sulfate, and concentrated. The yield of brown oil was 88.77 g and was used without further purification. Anal. Calcd. For C19H26N2O2S: C, 65.9; H, 7.6; N, 8.1; S, 9.3. Found: C, 66.20; H, 7.85; N, 8.60; S, 7.93.

Workup

  1. extractionThe oily precipitate was extracted with methylene chloride
  2. washthe extract was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customwas used without further purification

Sources & evidence

ORD record
ord-75850a36f1a24abb9732c11e16c87418
Source dataset
uspto-grants-2003_03
Patent number
US06528223B1

Reaction notes

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