Sodium Dithionite → HCID 57747382, compound

HRID 222085Notes

Reaction equation

HRID 222085 reaction equation
[O-]S(S([O-])=O)=O.[Na+].[Na+].[Br:9][C:10]1[CH:15]=[C:14]([CH3:16])[C:13]([S:17][C:18]2[C:23]([N+]([O-])=O)=[C:22](/[CH:27]=[CH:28]/[N:29](C)C)[N:21]=[C:20]([N:32]([C:40]3[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=3)[C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[N:19]=2)=[C:12]([CH3:48])[CH:11]=1>O.C1COCC1>[Br:9][C:10]1[CH:11]=[C:12]([CH3:48])[C:13]([S:17][C:18]2[C:23]3[NH:29][CH:28]=[CH:27][C:22]=3[N:21]=[C:20]([N:32]([C:40]3[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=3)[C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[N:19]=2)=[C:14]([CH3:16])[CH:15]=1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 57747434HCID 57747434, compound

Product 1

HCID 57747382HCID 57747382, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Na2S2O4 (230 mmol) in water (100 ml) is added to a solution of tert-butyl 4-(4-bromo-2,6-dimethylphenylthio)-6-((E)-2-(dimethylamino)vinyl)-5-nitropyrimidin-2-yl4-cyanophenylcarbamate (46 mmol) in THF (300 ml). The mixture is stirred at room temperature for 2 days and then concentrated. The residue is washed with water and extracted with ethyl acetate. The organic layer is concentrated and the product obtained by crystallization from a mixture of water and methanol.

Workup

  1. concentrationconcentrated
  2. washThe residue is washed with water
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer is concentrated
  5. customthe product obtained by crystallization from a mixture of water and methanol

Sources & evidence

ORD record
ord-abf0299216134cd090b31288af5e4858
Source dataset
uspto-grants-2012_06
Patent number
US08207178B2

Reaction notes

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