Dimethylformamide → HCID 15411307, compound

HRID 1292156Notes

Reaction equation

HRID 1292156 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=1)[CH:16]=[N:17][C:18]1[CH:28]=[CH:27][C:21]2[NH:22][C:23](=[O:26])[CH2:24][S:25][C:20]=2[CH:19]=1.CN(C=O)C.[BH4-].[Na+]>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=1)[CH2:16][NH:17][C:18]1[CH:28]=[CH:27][C:21]2[NH:22][C:23](=[O:26])[CH2:24][S:25][C:20]=2[CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 15411306HCID 15411306, compound

Product 1

HCID 15411307HCID 15411307, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-[3-(2-Quinolinylmethoxy)benzylidenamino]-3,4-dihydro-2H-1,4-benzothiazin-3-one (6.383 g, 15 mmol) obtained in Example 91 was dissolved in a mixed solvent consisting of 200 ml of DMF and 50 ml of MeOH, followed by the addition of 2.26 g (60 mmol) of NaBH4 in small portions. After the resultant mixture was stirred for 30 minutes at room temperature, the solvent was distilled off under reduced pressure. Water was added to the residue, followed by extraction with CHCl3. The extract was washed with water, dried over MgsO4 and then concentrated. The concentrate was recrystallized from MeOH-AcOEt, whereby 5.117 g of the title compound were obtained as white powder (yield: 79.8%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater was added to the residue
  3. extractionfollowed by extraction with CHCl3
  4. washThe extract was washed with water
  5. customdried over MgsO4
  6. concentrationconcentrated
  7. customThe concentrate was recrystallized from MeOH-AcOEt

Sources & evidence

ORD record
ord-72a03f1f63e24d76ad1fcb97b1df9e32
Source dataset
uspto-grants-1998_05
Patent number
US05756518

Reaction notes

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