1-Bromooctane → Tetrakis-(p-nitrophenylthio)-phthalic acid N-n-octylimide

HRID 1462275Notes

Reaction equation

HRID 1462275 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[C:12]([S:42][C:43]3[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][CH:44]=3)=[C:13]([S:32][C:33]3[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=3)[C:14]([S:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=3)=[C:15]3[C:20](=[O:21])[NH:19][C:17](=[O:18])[C:16]=23)=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60].C(=O)([O-])[O-:62].[K+].[K+]>CN(C)C=O>[CH2:53]([N:19]=[C:17]([OH:18])[C:16]1[C:15](=[C:14]([S:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[C:13]([S:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[C:12]([S:42][C:43]2[CH:44]=[CH:45][C:46]([N+:49]([O-:51])=[O:50])=[CH:47][CH:48]=2)[C:11]=1[S:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)[C:20]([OH:62])=[O:21])[CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60]

Participants

5

Reactant 3

HCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 20269595Tetrakis-(p-nitrophenylthio)-phthalimide

Product 1

HCID 136399292Tetrakis-(p-nitrophenylthio)-phthalic acid N-n-octylimide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1 g (1.32 millimols) of tetrakis-(p-nitrophenylthio)-phthalimide (prepared according to Example 10), 0.57 g (2.97 millimols) of 1-bromooctane, 0.68 g (4.96 millimols) of potassium carbonate and 10 ml of N,N-dimethylformamide are stirred at 25° C. for 5 hours. The mixture is concentrated and the residue is acidified and extracted with methylene chloride. After recrystallisation from toluene/cyclohexane, 1.02 g (89% of theory) of the title imide are obtained; melting point 202°-4° C.

Workup

  1. concentrationThe mixture is concentrated
  2. extractionextracted with methylene chloride
  3. customAfter recrystallisation from toluene/cyclohexane, 1.02 g (89% of theory) of the title imide
  4. customare obtained

Sources & evidence

ORD record
ord-a41dac47df0e4cf9bc37339bbccd7ca2
Source dataset
uspto-grants-1984_07
Patent number
US04459414

Reaction notes

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