1-Chloro-4-isocyanato-2-(trifluoromethyl) benzene → HCID 54394264, compound

HRID 1973928Notes

Reaction equation

HRID 1973928 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[F:8][C:9]([F:21])([F:20])[C:10]1[CH:11]=[C:12]([N:17]=[C:18]=[O:19])[CH:13]=[CH:14][C:15]=1[Cl:16]>C1C=CC=CC=1>[Cl:16][C:15]1[CH:14]=[CH:13][C:12]([NH:17][C:18]([N:1]=[C:2]2[CH2:6][CH2:5][CH2:4][N:3]2[CH3:7])=[O:19])=[CH:11][C:10]=1[C:9]([F:8])([F:20])[F:21]

Participants

4

Reactant 2

HCID 27332651-Chloro-4-isocyanato-2-(trifluoromethyl) benzeneHCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 54394264HCID 54394264, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The hydrochloride salt of 2 -imino-1 -methylpyrrolidine (6.73 g; 0.05 mole) is converted to free base by adding 5 ml. of 50 % NaOH and extracting into benzene. After drying over K2CO3, the benzene solution is stirred at room temperature and 11.08 g. (0.05 mole) of 3-trifluoromethyl- 4-chlorophenylisocyanate [prepared according to the method of K. Inukai and Y. Maki, Kogyo Kagaku Zasski, 70 (4), 491-4 (1967)] dissolved in about 50 ml. of anhydrous benzene is added dropwise to this solution. After one-half of the amount is added cloudiness occurs and then solid precipitates. The mixture is stirred at room temperature overnight. The solid is collected, 1-(4-chloro-3-trifluoromethylphenyl)-3-(1-methyl-2 -pyrrolidylidene)urea, and recrystallizations from ethyl acetate yields the pure product, m.p. = 175° C.

Workup

  1. additionby adding 5 ml
  2. extractionof 50 % NaOH and extracting into benzene
  3. dry with materialAfter drying over K2CO3
  4. additionAfter one-half of the amount is added cloudiness
  5. customsolid precipitates
  6. stirringThe mixture is stirred at room temperature overnight
  7. customThe solid is collected
  8. custom1-(4-chloro-3-trifluoromethylphenyl)-3-(1-methyl-2 -pyrrolidylidene)urea, and recrystallizations from ethyl acetate
  9. customyields the pure product, m.p. = 175° C.

Sources & evidence

ORD record
ord-c6fa5e1bdb344f50b3dcb07b15c13feb
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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