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

HRID 1721039Notes

Reaction equation

HRID 1721039 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-caa8b1d040ba4bec8a37c19e588ef899
Source dataset
uspto-grants-1996_04
Patent number
US05508415

Reaction notes

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