Dimethyl Sulfoxide → HCID 54375901, compound

HRID 1871159Notes

Reaction equation

HRID 1871159 reaction equation
[C:1]1([N:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[CH:14]=[C:13]([CH:18]=O)[CH:12]=[CH:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:26][C:27]1[S:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1.[OH-].[K+].CS(C)=O>O>[S:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=[C:27]1[CH:26]=[CH:18][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([N:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:17]=[CH:16]2

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 84462-MethylbenzothiazoleHCID 14797Potassium HydroxideHCID 18694821HCID 18694821, compound

Product 1

HCID 54375901HCID 54375901, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N,N-diphenyl-6-amino-2-naphthaldehyde (4.8 g, 0.015 mol.), 2-methyl benzothiazole (3.0 g, 0.020 mol.), powdered potassium hydroxide (18.0 g, 0.32 mol.) and DMSO (30 ml) was stirred at room temperature for 1 hour, poured into water, and the solids which separated were collected by filtration. These solids were purified by column chromatography on alumina using 1:3 toluene-heptane as the eluent, to give 3.6 g. of product (53% yield) m.p. 181.1-184.8° C. Recrystallization from 1:1 toluene-ethyl acetate raised the m. p. to 201.8-203.8° C. Mass Spec: m/z 454, (M+). Analysis calculated for C31H22N2S: C, 81.92; H, 4.88; N, 6.16; S, 7.04. Found: C, 81.82; H, 4.93; N; 6.04, and S; 6.91.

Workup

  1. customthe solids which separated
  2. filtrationwere collected by filtration
  3. customThese solids were purified by column chromatography on alumina using 1:3 toluene-heptane as the eluent
  4. customto give 3.6 g

Sources & evidence

ORD record
ord-27b47332d67a412aa2089bb3b9f42b70
Source dataset
uspto-grants-2000_08
Patent number
US06100405

Reaction notes

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