3-Fluorophenyl isocyanate → HCID 68122156, compound

HRID 2071518Notes

Reaction equation

HRID 2071518 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[F:8][C:9]1[CH:10]=[C:11]([N:15]=[C:16]=[O:17])[CH:12]=[CH:13][CH:14]=1>C1C=CC=CC=1>[OH2:17].[F:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]([N:1]=[C:2]2[CH2:6][CH2:5][CH2:4][N:3]2[CH3:7])=[O:17])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 1230643-Fluorophenyl isocyanateHCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 68122156HCID 68122156, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The hydrochloride salt of 2-imino-1-methylpyrrolidine is converted to free base (4.9 g.; 0.05 mole) in benzene in the usual manner. After drying over K2CO3, the benzene solution is stirred at room temperature and 6.86 g. (0.05 mole) of m-fluorophenylisocyanate, dissolved in anhydrous benzene, is added. Heat evolves and after 5-10 minutes, solid precipitates. Stirring is continued for one hour and the solid is then collected (m.p. = 142°-143° C.). Evaporation of solvent from the filtrate yields a second crop (m.p. =142°-143° C.). Recrystallization of the combined solids from ethyl acetate gives the product 1-m-fluorophenyl-3-(1-methyl-2-pyrrolidylidene)urea hydrate, m.p. = 142°-143° C.

Workup

  1. dry with materialAfter drying over K2CO3
  2. additionis added
  3. customsolid precipitates
  4. stirringStirring
  5. waitis continued for one hour
  6. customthe solid is then collected (m.p. = 142°-143° C.)
  7. customEvaporation of solvent from the filtrate
  8. customyields a second crop (m.p. =142°-143° C.)
  9. customRecrystallization of the combined solids from ethyl acetate

Sources & evidence

ORD record
ord-1e24ee4279d6418c8642de6e340e614a
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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