Carbon Dioxide → HCID 20449523, compound

HRID 358217Notes

Reaction equation

HRID 358217 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]=1.C(=O)=O>CC(C)=O>[N:5]([C:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:12]=2)[N:7]=1)=[C:1]=[S:2]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 10040ThiophosgeneHCID 477954,5-Dihydro-1-(3-(trifluoromethyl)phenyl)-1H-pyrazol-3-amine

Product 1

HCID 20449523HCID 20449523, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Thiophosgene (11.5 g) was added slowly to a solution of 3-amino-1-(3-trifluoromethylphenyl)-2-pyrazoline (23 g) (prepared according to Reference Example 1 of European patent specification No. 22-578) in acetone (250 ml) at 0° in an atmosphere of carbon dioxide. The addition was completed in about 20 minutes and was then allowed to warm to room temperature for 1 hour. The resulting insoluble solid, the hydrochloride of the starting base, was filtered off and washed with fresh acetone. The combined filtrate and washings were evaporated in vacuo to give crude 3-isothiocyanato-1-(3-trifluoromethylphenyl)-2-pyrazoline as a gum (13 g) which subsequently crystallised. This compound was used directly without purification but the presence of the isothiocyanate group was confirmed by infra red spectroscopy which exhibited a broad band in the region of 2005 cm-1. This gum (3.8 g) was suspended in toluene (40 ml) and stirred during the addition of butylamine (1.5 g). When the gum changed into a colourless solid. After 2 hours, the mixture was warmed to about 35° for 10 minutes and then cooled back to room temperature. The resulting solid was collected, washed with a little fresh toluene and recrystallised from propanol in long prisms, m.p. 197°-198° of 3-(3-butylthioureido)-1-(3-trifluoromethylphenyl)-2-pyrazoline.

Workup

  1. additionThe addition
  2. filtrationThe resulting insoluble solid, the hydrochloride of the starting base, was filtered off
  3. washwashed with fresh acetone
  4. customThe combined filtrate and washings were evaporated in vacuo

Sources & evidence

ORD record
ord-0da55f93100a4bc0bc3b18c5fdc7cff9
Source dataset
uspto-grants-1984_08
Patent number
US04465685

Reaction notes

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