Sodium Chloride → HCID 68052643, compound

HRID 1685129Notes

Reaction equation

HRID 1685129 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:4]=1[CH2:5][NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[N+:16]([O-])=O)[CH2:12][N:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[O:28][CH3:29])[CH2:10]2.S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH-].[NH4+].[OH-].[Na+].[Cl-].[Na+]>O.O1CCCC1>[CH3:1][O:2][C:3]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:4]=1[CH2:5][NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[NH2:16])[CH2:12][N:11]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=1[O:28][CH3:29])[CH2:10]2

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 24489Sodium DithioniteHCID 86651927HCID 86651927, compound

Product 1

HCID 68052643HCID 68052643, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N,2-bis(2,4-dimethoxybenzyl)-6-nitroisoindolin-5-amine T-03 (2.7 g, 5.6 mmol) and sodium hydrosulfite (15.6 g, 90 mmol) was added a solution of tetrahydrofuran (40 mL), water (40 mL) and ammonium hydroxide (40 mL). The reaction mixture was stirred at room temperature overnight. The reaction mixture was basified with sodium hydroxide and saturated with sodium chloride. The reaction mixture was filtered and extracted with ethyl acetate. The organic layer was dried over sodium sulfate. Solvent was evaporated under reduced pressure to afford the desired N5,2-bis(2,4-dimethoxybenzyl)isoindoline-5,6-diamine T-04 (2.5 g, 5.6 mmol). The crude product was used in the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customSolvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a6a1f82423ca4f9e9f97f68e8506e455
Source dataset
uspto-grants-2012_04
Patent number
US08148363B2

Reaction notes

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