Acetic Acid → HCID 86736555, compound

HRID 263062Notes

Reaction equation

HRID 263062 reaction equation
C(OC(=O)[C:5]([C:31]#[N:32])([N:13]=[N:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.C(O)(=O)C.Cl.C(=O)(O)[O-].[Na+]>O>[F:23][C:22]([F:24])([F:25])[C:21]([C:18]1[CH:17]=[CH:16][C:15]([NH:14][N:13]=[C:5]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:31]#[N:32])=[CH:20][CH:19]=1)([OH:30])[C:26]([F:27])([F:29])[F:28]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 54375678HCID 54375678, compound

Product 1

HCID 86736555HCID 86736555, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 238 mg. (0.5 mmol) of α-cyano-α-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenylazo]benzenepropanoic acid ethyl ester in 3 ml. of acetic acid and 1 ml. of concentrated hydrochloric acid was stirred at room temperature for 30 minutes, diluted with water, made basic with sodium bicarbonate and extracted with ether. The ether extracts were dried and concentrated. The residue was dissolved in 1:1 benzene-dichloromethane and passed over a little silica gel. The eluate was concentrated and crystallized from hexane to give α-[1-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]hydrazin-2-ylidene]benzenepropanenitrile Isomer A as yellow crystals, m.p. 90°-92°.

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether extracts were dried
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 1:1 benzene-dichloromethane
  5. concentrationThe eluate was concentrated
  6. customcrystallized from hexane

Sources & evidence

ORD record
ord-6da1511c8cb540f59ab26026e5497941
Source dataset
uspto-grants-1979_05
Patent number
US04156016

Reaction notes

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