Phosphorus oxychloride → HCID 58739136, compound

HRID 720235Notes

Reaction equation

HRID 720235 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:11]2[S:12][C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:14][C:10]=2[C:9](=O)[NH:8][N:7]=1)=[O:5])[CH3:2].P(Cl)(Cl)([Cl:25])=O>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[N:8][C:9]([Cl:25])=[C:10]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[S:12][C:11]=12)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58739134HCID 58739134, compound

Product 1

HCID 58739136HCID 58739136, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(4-fluoro-phenyl)-4-oxo-4,5-dihydro-thieno[2,3-d]pyridazine-7-carboxylic acid ethyl ester (0.2 g, mmol) in phosphorous oxychloride (3 mL) was heated at 90° C. for 3 hours, cooled and evaporated to dryness. To the residue was added ice and ethyl acetate and then basified over potassium carbonate solid. The organic layer was separeted, washed with water, brine and dried over sodium sulfate. The organic layer was evaporated to dryness and the residue was purified by flash chromatography (silica gel, 5% acetone/hexane) to obtain 4-chloro-2-(4-fluorophenyl)-thieno[2,3-d]pyridazine-7-carboxylic acid ethyl ester as a solid (0.12 g). MS: m/z=338 (M+1).

Workup

  1. temperaturecooled
  2. customevaporated to dryness
  3. additionTo the residue was added ice and ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customThe organic layer was evaporated to dryness
  7. customthe residue was purified by flash chromatography (silica gel, 5% acetone/hexane)

Sources & evidence

ORD record
ord-f07bbfca8166423784ea9b751db53faa
Source dataset
uspto-grants-2006_11
Patent number
US07135470B2

Reaction notes

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