4-Fluorophenyl isocyanate → HCID 54010928, compound

HRID 1973927Notes

Reaction equation

HRID 1973927 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[C:16]=[O:17])=[CH:11][CH:10]=1>C1C=CC=CC=1>[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:1]=[C:2]2[CH2:6][CH2:5][CH2:4][N:3]2[CH3:7])=[O:17])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 54010928HCID 54010928, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 4.9 g. (0.05 mole) of 2 -imino-1 -methylpyrrolidine in anhydrous benzene is added 6.85 g. (0.05 mole) of p-fluorophenylisocyanate, dissolved in anhydrous benzene, dropwise with stirring. The mixture is stirred at room temperature overnight, then filtered and the filtrate taken to dryness in vacuo. The residue is triturated with isopropanol. The solid which forms is collected, 1 -p-fluorophenyl-3 -(1 -methyl-2 -pyrrolidylidene)urea, m.p. = 113°-115° C. Recrystallization from ethyl acetate yields the pure product, m.p. = 115°-116° C.

Workup

  1. stirringThe mixture is stirred at room temperature overnight
  2. filtrationfiltered
  3. customThe residue is triturated with isopropanol
  4. customThe solid which forms is collected
  5. customRecrystallization from ethyl acetate
  6. customyields the pure product, m.p. = 115°-116° C.

Sources & evidence

ORD record
ord-4f9d183cfeb04da9886e0cf93fe3ae52
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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