Toluene → HCID 19760642, compound

HRID 249208Notes

Reaction equation

HRID 249208 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[C:30]1([CH3:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:22]([N:14]([CH2:36][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 7503Benzyl ChlorideHCID 7564N-Phenyl-p-phenylenediamineHCID 8471Triethylamine

Product 1

HCID 19760642HCID 19760642, compound

Procedure

A well-stirred mixture of N-phenyl-p-phenylenediamine (22.1 g, 0.12 mol) and triethylamine (26.7 g, 0.26 mol) in toluene (300 ml) is treated with benzyl chloride (30.4 g, 0.24 mol). The resulting mixture is warmed to 70°-75° C. for five hours, then cooled and washed with water. The organic fraction is concentrated to an oil that is chromatographed (silica gel; heptane:ethyl acetate) to give the title compound in a yield of 15 g (34%) as a yellow solid melting at 88°-90° C.

Workup

  1. temperatureThe resulting mixture is warmed to 70°-75° C. for five hours
  2. temperaturecooled
  3. washwashed with water
  4. concentrationThe organic fraction is concentrated to an oil that
  5. customis chromatographed (silica gel; heptane:ethyl acetate)

Sources & evidence

ORD record
ord-e5a4f59fb6be466c83d7530a4482912a
Source dataset
uspto-grants-1993_05
Patent number
US05213699

Reaction notes

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