p-Toluenesulfonic acid → HCID 86743955, compound

HRID 1084476Notes

Reaction equation

HRID 1084476 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4]([CH3:12])([CH3:11])[C:3]1=[CH2:13].[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([OH:24])(=[O:23])=[O:22])=[CH:17][CH:16]=1.[CH:25]([C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:28]=1[C:42]1[S:43][CH:44]=[CH:45][CH:46]=1)=O>C(OC(=O)C)(=O)C.C(OCC)(=O)C>[CH3:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([O-:24])(=[O:23])=[O:22])=[CH:19][CH:20]=1.[CH3:14][C:15]1[CH:16]=[CH:17][C:18]([S:21]([O-:24])(=[O:23])=[O:22])=[CH:19][CH:20]=1.[C:36]1([N:29]2[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:27]([CH:25]=[CH:13][C:3]3[C:4]([CH3:11])([CH3:12])[C:5]4[C:6]([N+:2]=3[CH3:1])=[N:7][CH:8]=[CH:9][CH:10]=4)=[C:28]2[C:42]2[S:43][CH:44]=[CH:45][CH:46]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1.[C:36]1([N:29]2[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:27]([CH:25]=[CH:13][C:3]3[C:4]([CH3:11])([CH3:12])[C:5]4[C:6]([N+:2]=3[CH3:1])=[N:7][CH:8]=[CH:9][CH:10]=4)=[C:28]2[C:42]2[S:43][CH:44]=[CH:45][CH:46]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1705131H-Pyrrolo[2,3-b]pyridine, 2,3-dihydro-1,3,3-trimethyl-2-methylene-HCID 20063544HCID 20063544, compound

Product 1

HCID 86743955HCID 86743955, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
135 °C

Procedure

A solution of 1.73 g of 1,3,3-trimethyl-2-methylene-pyrrolo[2,3-b]pyridine in 3 ml of acetic anhydride was added to a solution of 1.72 g anhydrous 4-methylbenzenesulfonic acid in 5 ml of acetic anhydride, followed by 3.04 g of 3-formyl-1-phenyl-2-(2-thiophenyl)indole. The resulting mixture was stirred and heated at 135° C. for 1 minute, then was diluted with 60 ml of ethyl acetate and cooled to 0°-5° C. The solid product was collected by suction filtration, washed with ethyl acetate, and was combined with a second amount of solid obtained from concentration of the filtrate to give 6.26 g of damp crystals. Recrystallization from a mixture of 20 ml acetone, 2 ml methanol, and 40 ml ethyl acetate gave 3.88 g (61% theoretical) of dye 2 (absorbance maximum in methanol, 505 nm; absorptivity, 62,200), determined to be 95% pure by high-performance liquid chromatography.

Workup

  1. temperaturecooled to 0°-5° C
  2. filtrationThe solid product was collected by suction filtration
  3. washwashed with ethyl acetate
  4. customobtained from concentration of the filtrate

Sources & evidence

ORD record
ord-8457b571d7e24cfab9207f26292770eb
Source dataset
uspto-grants-1991_04
Patent number
US05004812

Reaction notes

Loading…