1-Bromopropane → HCID 19033232, compound

HRID 266611Notes

Reaction equation

HRID 266611 reaction equation
[CH:1]1[C:18]2=[C:19]3[C:8]([C:9]4[C:20]5[C:13](=[CH:14][CH:15]=[CH:16][C:17]2=5)[CH:12]=[CH:11][CH:10]=4)=[CH:7][CH:6]=[C:5]2[C:21]([O:23][C:24](=[O:25])[C:3](=[C:4]23)[CH:2]=1)=[O:22].[CH3:26][C:27](C)([O-])[CH3:28].[K+].CN1C[CH2:36][CH2:35][C:34]1=[O:38].BrCCC>C(O)CC>[CH:7]1[C:8]2=[C:19]3[C:18]([C:17]4[C:20]5[C:13](=[CH:12][CH:11]=[CH:10][C:9]2=5)[CH:14]=[CH:15][CH:16]=4)=[CH:1][CH:2]=[C:3]([C:24]([O:38][CH2:34][CH2:35][CH3:36])=[O:25])[C:4]3=[C:5]([C:21]([O:23][CH2:26][CH2:27][CH3:28])=[O:22])[CH:6]=1

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 13387N-methyl-2-pyrrolidoneHCID 11759069Perylene-3,4-dicarboxylic anhydrideHCID 23665647Potassium tert-butoxide

Product 1

HCID 19033232HCID 19033232, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

0.18 g (0.56 mmol) of perylene-3,4-dicarboxylic anhydride is suspended in 10 ml of dried n-propanol, 0.15 g (1.43 mmol) of potassium t-butoxide is added, and the suspension is stirred at room temperature for 0.5 hour with the exclusion of moisture. During the course of the reaction, a colour change from brown to yellow can be observed, during which the precipitate dissolves. The solvent is then distilled off, and first 10 ml of N-methylpyrrolidone and then 0.20 ml (2.4 mmol) of 1-bromopropane are added, and the yellow solution is stirred at room temperature for 17 hours. The solvent is distilled off in vacuo, the yellow residue is chromatographed on silica gel using chloroform. Yield 0.16 g (68%), m.p. 253° C., Rf (CHCl3 /silica gel)=0.48. UV (CHCl3): λmax (ε)=460 nm (27944), 437 (23875), 340 (1900), 327 (2050), 260 (32991). Fluorescence (CHCl3):λmax (Irel)=482 nm (1), 509 (0.69), solid fluorescence: λmax =595 nm.

Workup

  1. customDuring the course of the reaction
  2. dissolutiondissolves
  3. distillationThe solvent is then distilled off
  4. stirringthe yellow solution is stirred at room temperature for 17 hours
  5. distillationThe solvent is distilled off in vacuo
  6. customthe yellow residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-e7e936f3c6cc4a34854fe76a6090aa61
Source dataset
uspto-grants-1997_07
Patent number
US05650513

Reaction notes

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