Formic Acid → HCID 12878255, compound

HRID 2166665Notes

Reaction equation

HRID 2166665 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[C:4]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]=1.C(O)=[O:31]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:31])[CH2:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])=[C:4]([C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 128782521-[4-Chloro-2-benzoylphenyl]-3-phthalimidopropyne

Product 1

HCID 12878255HCID 12878255, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 20 g (50 mmole) of 1-[4-chloro-2-benzoylphenyl]-3-phthalimidopropyne, 1.0 g (3 mmole) of mercuric sulfate and 55 ml of formic acid in 50 ml of methylene chloride was stirred at room temperature for 30 min. The mixture was poured over ice and extracted with ethyl acetate. The ethyl acetate solution was dried over anhydrous sodium sulfate and concentrated at reduced pressure to dryness. The residue was crystallized from a mixture of ethyl acetate and ether to give a colorless solid. Recrystallization from acetone gave colorless prisms, mp 163°-164° C.

Workup

  1. additionThe mixture was poured over ice
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  4. concentrationconcentrated at reduced pressure to dryness
  5. customThe residue was crystallized from a mixture of ethyl acetate and ether
  6. customto give a colorless solid
  7. customRecrystallization from acetone
  8. customgave colorless prisms, mp 163°-164° C.

Sources & evidence

ORD record
ord-aa7738c0849e4348890d8754ba187b6d
Source dataset
uspto-grants-1983_06
Patent number
US04388239

Reaction notes

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