1,3,3-Trimethyl-2-methyleneindoline → HCID 10873793, compound

HRID 1656124Notes

Reaction equation

HRID 1656124 reaction equation
[C:1]([O:6][CH2:7][C:8]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[C:10]([CH:11]=O)[C:9]=1[SH:19])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:20]=[C:21]1[C:29]([CH3:31])([CH3:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]1[CH3:32]>CC(=O)CC>[C:1]([O:6][CH2:7][C:8]1[C:9]2[S:19][C:21]3([C:29]([CH3:31])([CH3:30])[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]3[CH3:32])[CH:20]=[CH:11][C:10]=2[CH:13]=[C:14]([N+:16]([O-:18])=[O:17])[CH:15]=1)(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

4

Reactant 2

HCID 83511,3,3-Trimethyl-2-methyleneindolineHCID 109458763-Methacryloxymethyl-5-nitrothiosalicylaldehyde

Product 1

HCID 10873793HCID 10873793, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In 120 ml of 2-butanone were dissolved 14.1 g of 3-methacryloxymethyl-5-nitrothiosalicylaldehyde and 8.7 g of 2-methylene-1,3,3-trimethylindoline, and the solution was heated under reflux for 20 hours in a nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure, and the residue was purified by a silica gel column, giving 15.9 g of 8-methacryloxymethyl-6-nitro-1',3',3'-trimethylspiro[2H-1-benzothiopyran-2,2'-indoline] in the form of pale yellow crystals (yield 73%).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 20 hours in a nitrogen atmosphere
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-20d82bc80d3c429dbbe221a63ce11a2d
Source dataset
uspto-grants-1993_10
Patent number
US05252742

Reaction notes

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