1,3-Dichloro-2-isothiocyanatobenzene → N-(2,6-Dichlorophenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbothioamide

HRID 1886587Notes

Reaction equation

HRID 1886587 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[O:6][CH:7]1[CH2:10][NH:9][CH2:8]1.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[N:24]=[C:25]=[S:26].[N-]=C=S>C(O)C>[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[NH:24][C:25]([N:9]1[CH2:10][CH:7]([O:6][C:5]2[CH:11]=[CH:12][CH:13]=[C:3]([C:2]([F:1])([F:14])[F:15])[CH:4]=2)[CH2:8]1)=[S:26]

Participants

5

Reactant 3

HCID 1232391,3-Dichloro-2-isothiocyanatobenzeneHCID 111385383-[3-(Trifluoromethyl)phenoxy]azetidineHCID 178418790HCID 178418790, compound

Product 1

HCID 15053384N-(2,6-Dichlorophenyl)-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbothioamideYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.04 mole of 3-[3-(trifluoromethyl) phenoxy]azetidine in 100 ml of absolute ethanol was stirred in a tap water bath while 8.16 g (0.04 mole) of 2,6-dichlorophenyl isothiocyanate was added all at once. The reaction was slightly exothermic and as the isothiocyanate began to dissolve, product began to precipitate. After stirring for 45 minutes the reaction mixture was heated on a steam bath to assure that all the isothiocyanate dissolved, and upon cooling, filtration yielded 15.2 g of white crystalline product. A portion of this material (7.9 g) was recrystallized from absolute ethanol to give 4.3 g of pure crystalline powder, m.p. 196°-197° C.

Workup

  1. additionwas added all at once
  2. dissolutionto dissolve
  3. customto precipitate
  4. temperaturewas heated on a steam bath
  5. dissolutiondissolved
  6. temperatureupon cooling
  7. filtrationfiltration

Sources & evidence

ORD record
ord-71a098fb118844b18a444e4fc06bf0f7
Source dataset
uspto-grants-1992_09
Patent number
US05151418

Reaction notes

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