Triethylamine → 2-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazoline

HRID 5312

Reaction equation

HRID 5312 reaction equation
Cl.[NH:2]=[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:6]=[C:5]([CH3:18])[S:4]1.C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.[F:38][CH:39]([F:43])[C:40](O)=[O:41]>C(Cl)(Cl)Cl>[F:38][CH:39]([F:43])[C:40]([N:2]=[C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)[CH:6]=[C:5]([CH3:18])[S:4]1)=[O:41]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9788Difluoroacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 214800712-Imino-3-(3-trifluoromethyl-phenyl)-5-methylthiazoline hydrochloride

Product 1

HCID 110889832-Difluoroacetylimino-3(3-trifluoromethylphenyl)-5-methylthiazolineYield 62.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-imino-3-(3-trifluoromethylphenyl)-5-methylthiazoline hydrochloride (0.42 g), triethylamine (2.2 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.8 g) and difluoroacetic acid (0.75 g) in chloroform (10 ml) was refluxed for 8 hours. The residue was washed with aqueous hydrochloric acid and aqueous potassium carbonate and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was subjected to column chromatography to give 2-difluoroacetylimino-3-(3-trifluoromethylphenyl)-5-methylthiazoline (Compound No. 63) (0.3 g). m.p., 117.9° C.

Workup

  1. temperaturewas refluxed for 8 hours
  2. washThe residue was washed with aqueous hydrochloric acid and aqueous potassium carbonate
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8c02e4c5d0114a13a64c527fd72cc67f
Source dataset
uspto-grants-1993_09
Patent number
US05244863

Linked notes

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