Carbon Dioxide → HCID 13922904, compound

HRID 2232346Notes

Reaction equation

HRID 2232346 reaction equation
Cl.[NH2:2][C:3]1[CH:11]=[CH:10][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+].C(=O)=O>CS(C)=O>[CH2:12]([N:2]([CH2:9][C:5]1[CH:6]=[CH:10][CH:11]=[CH:3][CH:4]=1)[C:3]1[CH:11]=[CH:10][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 1633601296803-46-2

Product 1

HCID 13922904HCID 13922904, compoundYield 121.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A stirred solution of 5-aminobenzo[b]thiophene hydrochloride (4.65 g, 0.025 mole) in dry DMSO (40 ml) was treated with benzyl bromide (6 ml, 0.05 mole) followed by solid NaHCO3 (6.3 g, 0.075 mole). After the immediate, vigorous evolution of CO2, the mixture set to a solid mass. This was held at ambient temperature overnight and the solid then was collected and recrystallized from CH3CN to obtain 5.0 g (61%) of 5-(dibenzyl)aminobenzo[b]thiophene, m.p. 114°-117° C. A sample recrystallized from ethyl acetate-hexane melted at 115°-117° C.

Workup

  1. customthe solid then was collected
  2. customrecrystallized from CH3CN

Sources & evidence

ORD record
ord-0fb7ac1a000a426abe667b55ee9b73bc
Source dataset
uspto-grants-1988_11
Patent number
US04788192

Reaction notes

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