3-Bromo-2-methyl-1-propene → 2-(2-methyl-4-nitrophenylimino)-3-(2-methyl-prop-2-enyl)-4,4-dimethyl-1,3-thiazolidine HBr salt

HRID 276295Notes

Reaction equation

HRID 276295 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[NH:16][C:15]([CH3:18])([CH3:17])[CH2:14][S:13]1.[CH3:19][C:20](=[CH2:23])[CH2:21][Br:22]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[NH:16][C:15]([CH3:18])([CH3:17])[CH2:14][S:13]1.[BrH:22].[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[N:16]([CH2:21][C:20]([CH3:23])=[CH2:19])[C:15]([CH3:18])([CH3:17])[CH2:14][S:13]1

Participants

5

Reactant 2

HCID 3577853-Bromo-2-methyl-1-propeneHCID 178428743HCID 178428743, compound

Product 2

HCID 865901702-(2-methyl-4-nitrophenylimino)-3-(2-methyl-prop-2-enyl)-4,4-dimethyl-1,3-thiazolidine HBr saltYield 379.7%HCID 178428743HCID 178428743, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-(2-methyl-4-nitrophenylimino)-4,4-dimethyl-1,3-thiazolidine was prepared in a manner analogous to that described in Method C1a. To a suspension of 2-(2-methyl-4-nitrophenylimino)-4,4-dimethyl-1,3-thiazolidine (1.5 mmol) in toluene (10 mL) was added 2-methylprop-2-en-1-yl bromide (4.5 mmol) and the reaction mixture was heated at the reflux temp. for 3 h at which time the reaction was judged complete by TLC. The resulting precipitate was filtered at 50 ° C. The collected solids were washed with toluene (20 mL) and CH2Cl2 (20 mL) to yield 2-(2-methyl-4-nitrophenylimino)-3-(2-methyl-prop-2-enyl)-4,4-dimethyl-1,3-thiazolidine HBr salt (1.14 g, 77%): mp 229° C.

Workup

  1. temperaturethe reaction mixture was heated at the reflux temp
  2. filtrationThe resulting precipitate was filtered at 50 ° C
  3. washThe collected solids were washed with toluene (20 mL) and CH2Cl2 (20 mL)

Sources & evidence

ORD record
ord-4c847d54e0494823ba589a6adc30aa7f
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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