Benzyl Chloride → Benzyldiphenylamine

HRID 1614431Notes

Reaction equation

HRID 1614431 reaction equation
[CH2:1](OC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)C1C=CC=CC=1>O>[C:22]1([N:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11487DiphenylamineHCID 70352Benzyl Phenyl Ether

Product 1

HCID 69080Benzyldiphenylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-phenylbenzaldimine (1.81 g, 0.010 mol) and benzylphenyl ether (1.84 g, 0.010 mol) were heated at 75° C. in Na/DMF solution (2.0 g: 50 mL) for 30 minutes. The solution was then poured in 200 mL of water, the precipitate was filtered washed with water and dried. Recrystallization from methanol, 70 mL, gave white needles (73% isolated) mp 88°-90° C. (lit mp 86°-7° C.8, 88°-9° C.9). No depression in melting point occurred when this material was admixed with an authentic sample prepared from diphenylamine and benzyl chloride.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customdried
  4. customRecrystallization from methanol, 70 mL
  5. customgave white
  6. customneedles (73% isolated) mp 88°-90° C. (lit mp 86°-7° C.8, 88°-9° C.9)

Sources & evidence

ORD record
ord-84fcef409bc740b69a490c1957878580
Source dataset
uspto-grants-1993_03
Patent number
US05196606

Reaction notes

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