Formic Acid → HCID 15580708, compound

HRID 543808Notes

Reaction equation

HRID 543808 reaction equation
FC(F)(F)[C:3]([NH:5][C:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14](C(=O)C(F)(F)F)=[CH:13][CH:12]=2)[N:7]=1)=[O:4].C(O)=O.ClC1C=C(N2CC(C)C(NC=O)=N2)C=CC=1Cl>O>[C:11]1([N:8]2[CH2:9][CH2:10][C:6]([NH:5][CH:3]=[O:4])=[N:7]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 15580703HCID 15580703, compoundHCID 15580721HCID 15580721, compound

Product 1

HCID 15580708HCID 15580708, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.0 g. of 3-amino-1-phenyl-2-pyrozoline (prepared in Example 8) and 50.0 ml. of a mixture of formic acid and acetic anhydride (Example 15) is allowed to stand at room temperature for 3 hours. Water is added and the white crystals are collected by filtration. The solid is dissolved in dichloromethane. The solution is dried over magnesium sulfate and filtered through a hydrous magnesium silicate. The filtrate is evaporated in vacuo to give pink crystals. A 500 mg. portion of crude product is recrystallized from dichloromethane-hexane to give 403 mg. of the desired product as a white solid, m.p. 140°-141° C.

Workup

  1. additionA mixture of 10.0 g
  2. filtrationthe white crystals are collected by filtration
  3. dissolutionThe solid is dissolved in dichloromethane
  4. dry with materialThe solution is dried over magnesium sulfate
  5. filtrationfiltered through a hydrous magnesium silicate
  6. customThe filtrate is evaporated in vacuo
  7. customto give pink crystals
  8. customportion of crude product is recrystallized from dichloromethane-hexane
  9. customto give 403 mg

Sources & evidence

ORD record
ord-03c554fcc0d24db9ac2b3c70468e5725
Source dataset
uspto-grants-1984_05
Patent number
US04447442

Reaction notes

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