Phosphorus oxychloride → HCID 15408578, compound

HRID 1416958Notes

Reaction equation

HRID 1416958 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=O)[CH:11]=[CH:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:12]1[CH:11]=[CH:10][C:9]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:13]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 15408577HCID 15408577, compound

Product 1

HCID 15408578HCID 15408578, compound

Conditions

Temperature
200 °C

Procedure

A mixture of 1.00 g (2.92 mMol) of 6-(4-fluorophenyl)-1,2-dihydro-5-[4-(methylsulfonyl)phenyl]-2-oxopyridine from Step 8 and 25 ml of phosphorous oxychloride was heated in a bomb to 200° C. and maintained for 3 hours. After cooling, the mixture was evaporated to dryness. Chromatography of the residue over silica gel using 50% ethyl acetate/hexane as eluent gave 2-chloro-6-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyridine (211 mg) as a pure white crystalline solid: m.p. 192° C. (DSC). Anal. Calc'd for C18H13ClFNO2S·.1/4 H2O (MW 366.33): C, 59.02; H, 3.58; N, 3.82. Found: C, 58.68; H, 3.65; N, 3.86.

Workup

  1. temperaturemaintained for 3 hours
  2. temperatureAfter cooling
  3. customthe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-50ed7e4828014232824458521705a21b
Source dataset
uspto-grants-1999_06
Patent number
US05916905

Reaction notes

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