Hydrochloric Acid → Halofenate

HRID 1606596Notes

Reaction equation

HRID 1606596 reaction equation
FC(F)(F)C1C=C(C=CC=1)OC([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)C#N.C(NCCO)(=O)C.Cl.Cl.[F:31][C:32]([F:59])([F:58])[C:33]1[CH:34]=[C:35]([CH:55]=[CH:56][CH:57]=1)[O:36][C:37](=NC1C=CC(Cl)=CC=1)[C:38]([O:40][CH2:41][CH2:42][NH:43][C:44](=[O:46])[CH3:45])=[O:39]>CN(C)C=O.O.C(Cl)Cl>[F:59][C:32]([F:31])([F:58])[C:33]1[CH:34]=[C:35]([CH:55]=[CH:56][CH:57]=1)[O:36][CH:37]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:38]([O:40][CH2:41][CH2:42][NH:43][C:44](=[O:46])[CH3:45])=[O:39]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8880AcetylethanolamineHCID 22767844HCID 22767844, compoundHCID 86733344HCID 86733344, compound

Product 1

HCID 33584HalofenateYield 25%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(3-Trifluoromethylphenoxy)(4-chlorophenyl)acetonitrile is added to a solution of 2-acetamidoethanol (20.6 g., 0.2 mole) in anhydrous dimethylformamide (25 ml.). The reaction mixture is cooled to -10°C. and saturated with hydrogen chloride (50 g., 1.37 mole) and stirred for 5 hours at -10° to 0°C. To this reaction mixture containing 2-acetamidoethyl (3-trifluoromethylphenoxy)(4-chlorophenyl)iminoacetate hydrochloride is added methylene chloride (200 ml.) and then water (100 ml.). The organic layer is collected, washed with water (2 × 100 ml.) and then dried over magnesium sulfate. The dried solution is decolorized with carbon, filtered and then slowly diluted with hexane (1 liter) to afford 10.7 g. (25% yield) of 2-acetamidoethyl (3-trifluoromethylphenoxy)(4-chlorophenyl)acetate, m.p. 93°-95°C.

Workup

  1. customThe organic layer is collected
  2. washwashed with water (2 × 100 ml.)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. additionslowly diluted with hexane (1 liter)
  6. customto afford 10.7 g

Sources & evidence

ORD record
ord-8d106b0e4d48417990e3581a585136fe
Source dataset
uspto-grants-1976_04
Patent number
US03953490

Reaction notes

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