Sodium Hydroxide → HCID 22624060, compound

HRID 278954Notes

Reaction equation

HRID 278954 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[S:4].[CH2:7]([O:14][N:15]1[C:24](=[O:25])[C:23]2[CH:26]=[C:27]([OH:29])[CH:28]=[C:21]3[C:22]=2[C:17](=[CH:18][CH:19]=[CH:20]3)[C:16]1=[O:30])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+]>CN(C=O)C.O>[CH3:1][N:2]([CH3:6])[C:3]([O:29][C:27]1[CH:28]=[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:22]2=[C:23]([CH:26]=1)[C:24](=[O:25])[N:15]([O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:16]3=[O:30])=[S:4]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 27871Dimethylthiocarbamoyl chlorideHCID 22624014HCID 22624014, compound

Product 1

HCID 22624060HCID 22624060, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of excess dimethylthiocarbamoyl chloride in DMF (20 mL) was added to a mixture of 2-benzyloxy-5-hydroxy-benzo[de]isoquinoline-1,3-dione (3.5 g, 11.0 mmol) and sodium hydroxide (0.9 g, 22 mmol) in water (50 mL) at 0° C. The mixture was stirred vigorously at room temperature for 2 hours. The solid formed was filtered, washed with water, and dried. The crude product (0.5 g) was purified by column chromatography (silica gel using 2% methanol in chloroform). Fractions containing the target compound were combined, concentrated, and recrystallized from chloroform:ether mixture to give 0.3 g of the title compound, mp 211-214° C.;

Workup

  1. customThe solid formed
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried
  5. customThe crude product (0.5 g) was purified by column chromatography (silica gel using 2% methanol in chloroform)
  6. additionFractions containing the target compound
  7. concentrationconcentrated
  8. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-b28c0ab2a9b749669d8b184871225b38
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

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