[2-[3,5-Bis(chloromethyl)pyrazol-1-yl]-5-nitrophenyl]-phenylmethanone → [2-[3,5-bis(Phthalimidomethyl)pyrazol-1-yl]-5-nitrophenyl]phenylmethanone

HRID 66241Notes

Reaction equation

HRID 66241 reaction equation
Cl[CH2:2][C:3]1[CH:7]=[C:6]([CH2:8]Cl)[N:5]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:20])[N:4]=1.[C:27]1(=[O:37])[NH:31][C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12.[K]>CN(C=O)C>[C:27]1(=[O:37])[N:31]([CH2:2][C:3]2[CH:7]=[C:6]([CH2:8][N:31]3[C:30](=[O:32])[C:29]4=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]4[C:27]3=[O:37])[N:5]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=3[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:20])[N:4]=2)[C:30](=[O:32])[C:29]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:28]12

Participants

4

Reactant 2

HCID 12377538[2-[3,5-Bis(chloromethyl)pyrazol-1-yl]-5-nitrophenyl]-phenylmethanoneHCID 24194345Phthalimide potassium salt

Product 1

HCID 12377539[2-[3,5-bis(Phthalimidomethyl)pyrazol-1-yl]-5-nitrophenyl]phenylmethanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 12.8 g. (32.8 mmol) of the end product of Example 24, 18.5 g. (100 mmol) of potassium phthalimide, and 250 ml. of DMF was stirred and heated at 65° for 18 hours. After cooling, the mixture was poured over ice, washed with dil. brine, dried (MgSO4) and concentrated in vacuo. The residue was filtered through silica gel using EtOAc as an eluent. Removal of the solvent left the end product as a pale yellow solid, mp. 220°-224°. The analytical sample was prepared by recrystallization from acetone-hexane: pale yellow needles, mp 225°-226.5°.

Workup

  1. additionA mixture of 12.8 g
  2. temperatureheated at 65° for 18 hours
  3. temperatureAfter cooling
  4. additionthe mixture was poured over ice
  5. washwashed with dil. brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. filtrationThe residue was filtered through silica gel
  9. customRemoval of the solvent
  10. waitleft the end product as a pale yellow solid, mp. 220°-224°
  11. customThe analytical sample was prepared by recrystallization from acetone-hexane

Sources & evidence

ORD record
ord-e7bd8b3aca9e4e789df4aefeff8d0b99
Source dataset
uspto-grants-1978_12
Patent number
US04130716

Reaction notes

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