Phosphorus oxychloride → HCID 15907971, compound

HRID 2224044Notes

Reaction equation

HRID 2224044 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([C@@:8]12[CH2:25][CH2:24][C:23]3[CH:22]=[C:21]([O:26][CH3:27])[CH:20]=[CH:19][C:18]=3[C@H:17]1[CH:16](O)[CH2:15][C@@:13]1([CH3:14])[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)#[N:7].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[C:6]([C@@:8]12[CH2:25][CH2:24][C:23]3[CH:22]=[C:21]([O:26][CH3:27])[CH:20]=[CH:19][C:18]=3[C:17]1=[CH:16][CH2:15][C@@:13]1([CH3:14])[C@H:9]2[CH2:10][CH2:11][C@@H:12]1[O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)#[N:7]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 69105088HCID 69105088, compound

Product 1

HCID 15907971HCID 15907971, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

27.6 ml of phosphorus oxychloride was added in drops to a solution of 27.6 g of 4 in 275 ml of pyridine at a temperature of 0-5° C., and it was stirred for another 1.5 hours at this temperature. Then, the mixture was moved into a dropping funnel and added in drops to an ice-cooled, saturated sodium bicarbonate solution. Then, it was extracted with dichloromethane, the collected organic phases were washed with brine, dried on magnesium sulfate, and the solvent was removed in a vacuum. In this way, 23.5 g (89%) of almost colorless, foamy 5 was obtained, which was used without further purification in the next stage.

Workup

  1. customThen, the mixture was moved into a dropping funnel
  2. temperaturecooled
  3. extractionThen, it was extracted with dichloromethane
  4. washthe collected organic phases were washed with brine
  5. customdried on magnesium sulfate
  6. customthe solvent was removed in a vacuum
  7. customIn this way, 23.5 g (89%) of almost colorless, foamy 5 was obtained
  8. customwhich was used without further purification in the next stage

Sources & evidence

ORD record
ord-98a87ce172c440babe195a96c6dbab0f
Source dataset
uspto-grants-2008_05
Patent number
US07378404B2

Reaction notes

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