Dimethylformamide → HCID 15411307, compound

HRID 1418872Notes

Reaction equation

HRID 1418872 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. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe concentrate was recrystallized from MeOH-AcOEt

Sources & evidence

ORD record
ord-4d7339e5c1f046b5a6324154c8c17063
Source dataset
uspto-grants-1999_03
Patent number
US05885987

Reaction notes

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