4,4'-Dioctyldiphenylamine → HCID 20534322, compound

HRID 1388975Notes

Reaction equation

HRID 1388975 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[C:10]([C:15]([OH:17])=O)=[N:11][CH:12]=[CH:13][N:14]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:38][CH:37]=2)=[CH:31][CH:30]=1.C(OC(=O)C)(=O)C>>[CH3:20][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([C:7]2([N:35]([C:36]3[CH:37]=[CH:38][C:39]([CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH3:49])=[CH:40][CH:41]=3)[C:32]3[CH:31]=[CH:30][C:29]([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH3:21])=[CH:34][CH:33]=3)[C:9]3=[N:14][CH:13]=[CH:12][N:11]=[C:10]3[C:15](=[O:17])[O:8]2)=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 75694,4'-DioctyldiphenylamineHCID 7918Acetic AnhydrideHCID 20534325HCID 20534325, compound

Product 1

HCID 20534322HCID 20534322, compound

Procedure

A mixture containing 0.7 g. of 3-[4-(dimethylamino)benzoyl]-2-pyrazinecarboxylic acid, 1.0 g. of 4,4'-dioctyldiphenylamine and 7 ml. of acetic anhydride was stirred and gently heated in a warm water bath for one hour. The product, 7-[4-(dimethylamino)phenyl]-7-[bis(4-octylphenyl)amino]furo-[3,4-b]pyrazine-5(7H)-one was isolated by column chromatography as a rust-colored solid, m.p. 158°-168° C. A toluene solution of the product contacted with acidic clay or phenolic resin developed a reddish-brown image.

Workup

  1. additionA mixture containing 0.7 g
  2. temperaturegently heated in a warm water bath for one hour

Sources & evidence

ORD record
ord-28932c5a9a6e4eecb57ce2be157a59d2
Source dataset
uspto-grants-1981_01
Patent number
US04243250

Reaction notes

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