4-Fluorophenyl isocyanate → HCID 54010928, compound

HRID 2071495Notes

Reaction equation

HRID 2071495 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-b9815f78d8c44ab5b1c0c038c53f7569
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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