Dimethylformamide → HCID 21406361, compound

HRID 972206Notes

Reaction equation

HRID 972206 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].C(N(CC)CC)C.CN(C)C=O.[CH2:29](Br)[CH:30]=[CH2:31]>O>[CH2:31]([O:8][C:7]1[C:6]([Cl:9])=[CH:5][C:4]([C:10]2[CH:11]=[CH:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:3][C:2]=1[Cl:1])[CH:30]=[CH2:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 8471TriethylamineHCID 136315062HCID 136315062, compound

Product 1

HCID 21406361HCID 21406361, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4.9 g. of 6-(3,5-dichloro-4-hydroxyphenyl)-3-(2H)pyridazinone obtained in Example 5 and 2 g. of triethylamine in 30 ml. of dimethylformamide was added dropwise 2.4 g. of allyl bromide at 50° C. while stirring. The mixture was stirred at 50° C. for further 5 hours. After cooling, the reaction mixture was poured into 200 ml. of water and allowed to stand for a while. White solid substance thus formed was recovered by filtration, washed with water, dried to give 3.6 g. of crude crystalline substance, which was then recrystallized from methanol to give 3.2 g. of the desired product as colorless needles of m.p. 214° - 215° C.

Workup

  1. additionTo a mixture of 4.9 g
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured into 200 ml
  4. customWhite solid substance thus formed
  5. filtrationwas recovered by filtration
  6. washwashed with water
  7. customdried
  8. customto give 3.6 g
  9. customof crude crystalline substance, which was then recrystallized from methanol
  10. customto give 3.2 g

Sources & evidence

ORD record
ord-c86cfe6af83d4b659e775365733b833d
Source dataset
uspto-grants-1977_10
Patent number
US04052395

Reaction notes

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