Phosphorus oxychloride → HCID 53908445, compound

HRID 1721867Notes

Reaction equation

HRID 1721867 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH3:6][N:7]([CH:9]=[N:10][C:11]1[N:16]=[C:15](O)[C:14]([S:18]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])=[O:19])=[CH:13][N:12]=1)[CH3:8]>C(OCC)C>[Cl:3][C:15]1[C:14]([S:18]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])=[O:19])=[CH:13][N:12]=[C:11]([N:10]=[CH:9][N:7]([CH3:8])[CH3:6])[N:16]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178484253HCID 178484253, compound

Product 1

HCID 53908445HCID 53908445, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

POCl3 (1600 mL, 17.2M) was added gradually to mechanically stirred solid 2-[[(dimethylamino)methylene]amino]-4-hydroxy-N-(1,1-dimethylethyl)-5-pyrimidinesulfonamide (363 g, 1.20M). An exotherm was noted. The thick slurry was heated to reflux for 15 minutes. Upon cooling, ethyl ether was added and the precipitate filtered off. The resulting solid was suspended in water and treated with NaHCO3 (solid) to pH ~7.5. After extraction with methylene chloride, drying (MgSO4), and concentration, a yellow solid was obtained. Trituration with ethyl ether afforded a light-yellow compound. Upon drying at 40° C. in vacuo for 16 hours the desired compound (333 g, yield 87.0%, m.p. 178°-182° C.) was obtained.

Workup

  1. temperatureThe thick slurry was heated
  2. temperatureto reflux for 15 minutes
  3. temperatureUpon cooling
  4. filtrationthe precipitate filtered off
  5. additiontreated with NaHCO3 (solid) to pH ~7.5
  6. extractionAfter extraction with methylene chloride
  7. customdrying
  8. concentration(MgSO4), and concentration
  9. customa yellow solid was obtained

Sources & evidence

ORD record
ord-f4413f685e46417da0380b2c50bcd6f5
Source dataset
uspto-grants-1989_08
Patent number
US04853389

Reaction notes

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