Dimethyl Sulfoxide → HCID 18694828, compound

HRID 1871160Notes

Reaction equation

HRID 1871160 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]3C(=CC=2)C=C(C=O)C=[CH:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1S.[CH3:34][S:35]([CH3:37])=O>O>[S:35]1[C:37]2[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=2[N:7]=[C:34]1[C:28]1[CH:29]=[C:30]2[C:31](=[CH:32][CH:27]=1)[C:8]([N:7]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:9][CH:10]=[CH:11]2

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 87132-AminothiophenolHCID 18694821HCID 18694821, compound

Product 1

HCID 18694828HCID 18694828, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of N,N-diphenyl-6-amino-2-naphthaldehyde, (3.98 g., 0.0123 mol.), 2-aminothiophenol (1.5 ml, 0.014 mol.) and DMSO (20 ml) was heated to 180° C., held at this temperature for 45 minutes, and poured into water. The separated greenish solids were collected, air dried, transferred to a column of silica gel and eluted with 2:1 toluene-heptaneto get the product, 3.91 g. (74% yield), m.p. 186.1-187.3° C. Recrystallization from 1:1 toluene-heptane raised the m.p. to 188.1-189.5° C. Mass Spec: m/z 428 (M+). Analysis calculated for C29H20N2S: C, 81.29; H, 4.70; N, 6.54; S, 7.47. Found: C, 81.04; H, 4.88; N, 6.62; S, 7.31.

Workup

  1. customThe separated greenish solids were collected
  2. customair dried
  3. washeluted with 2:1 toluene-heptaneto
  4. customget the product, 3.91 g
  5. customRecrystallization from 1:1 toluene-heptane
  6. temperatureraised the m.p. to 188.1-189.5° C

Sources & evidence

ORD record
ord-a7a07a2a56ad4c7aaad1efabd2ff8be0
Source dataset
uspto-grants-2000_08
Patent number
US06100405

Reaction notes

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