Phenyl isocyanate → HCID 20304011, compound

HRID 1732622Notes

Reaction equation

HRID 1732622 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5](C=[CH:13][C:14]=1[CH3:15])[CH2:6][C:7]1[NH:8][CH2:9][CH2:10][N:11]=1.CC1CCCN(C)C1(C)C.[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[OH-].[K+]>C(Cl)(Cl)Cl>[C:26]1([NH:32][C:33]([N:8]2[CH2:9][CH2:10][N:11]=[C:7]2[C:6]2[CH:5]=[CH:4][C:3]([CH3:2])=[C:14]([CH3:13])[CH:15]=2)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 14797Potassium HydroxideHCID 187617721,2,2,3-TetramethylpiperidineHCID 20304020HCID 20304020, compound

Product 1

HCID 20304011HCID 20304011, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

2-(3,4-Dimethylbenzyl)-2-imidazoline hydrochloride (3.43 g; 0.01 mole) was suspended in dry chloroform (50 ml). The so obtained mixture was treated with tetramethylpiperidine (1.41 g; 0.01 mole) in dry chloroform (20 ml) and stirred at ambient temperature for approximately 4 hours with intermittent shaking, any large pieces of solid being broken up by means of a glass rod. Phenylisocyanate (1.20 g; 0.01 mole) in dry chloroform (10 ml) was then added dropwise to the cooled reaction mixture and the resulting mixture stirred overnight at ambient temperature. The solvent was evaporated under reduced pressure, the residue shaken up with water (60 to 100 ml) and filtered. The white solid so obtained was then transferred to a vacuum dessicator over fresh potassium hydroxide and left until the material had a constant melting point, to give 1-N-phenylcarbamoyl-2-(3,4-dimethylphenyl)-2-imidazoline, m.p. 139°-142° C. The 1H NMR spectrum was consistent with the assigned structure.

Workup

  1. customThe so obtained mixture
  2. stirringthe resulting mixture stirred overnight at ambient temperature
  3. customThe solvent was evaporated under reduced pressure
  4. stirringthe residue shaken up with water (60 to 100 ml)
  5. filtrationfiltered
  6. customThe white solid so obtained
  7. waitleft until the material

Sources & evidence

ORD record
ord-9f1f18bfafc84558b05ffd6f877d9bb0
Source dataset
uspto-grants-1980_12
Patent number
US04238497

Reaction notes

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