Phosphorus oxychloride → 3-(6-Chloro-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide

HRID 1097318Notes

Reaction equation

HRID 1097318 reaction equation
[CH3:1][NH:2][C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:11]=[N:12][NH:13][C:14](=O)[CH:15]=2)[CH:5]=1.O=P(Cl)(Cl)[Cl:20]>>[Cl:20][CH:14]1[NH:13][N:12]=[CH:11][C:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([NH:2][CH3:1])=[O:17])=[CH:15]1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 59443494N-Methyl-3-(6-oxo-1,6-dihydro-pyridazin-4-yl)-benzamide

Product 1

HCID 594434963-(6-Chloro-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide

Conditions

Temperature
110 °C

Procedure

N-Methyl-3-(6-oxo-1,6-dihydro-pyridazin-4-yl)-benzamide (1 eq, 3.14 mmol, 720 mg) is suspended in POCl3 (10 ml) and the reaction mixture is heated at 110° C. for 2 h. After cooling to room temperature, the solvent is removed in vacuo and then ice water is added. The pH is adjusted to pH8 with portionwise addition of sat. aqueous Na2CO3. The aqueous layer is extracted with EtOAc and the combined organic layers are washed with brine, dried over MgSO4, filtered and evaporated to dryness to yield 3-(6-Chloro-1,6-dihydro-pyridazin-4-yl)-N-methyl-benzamide as a yellow solid which did not require further purification; [M+H]+=248

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent is removed in vacuo
  3. additionice water is added
  4. additionThe pH is adjusted to pH8 with portionwise addition of sat. aqueous Na2CO3
  5. extractionThe aqueous layer is extracted with EtOAc
  6. washthe combined organic layers are washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-0f611b17aaa44e1a9c985430d4cc18b3
Source dataset
uspto-grants-2012_03
Patent number
US08143253B2

Reaction notes

Loading…