Water → HCID 57198983, compound

HRID 1825728Notes

Reaction equation

HRID 1825728 reaction equation
C[O-].[Na+].[CH3:4][C:5]1[CH:15]=[CH:14][C:8]2[NH:9][C:10](=[O:13])[CH2:11][S:12][C:7]=2[CH:6]=1.[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH:25]=O)=[CH:17]1.O>CN(C=O)C>[NH:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH:25]=[C:11]2[C:10](=[O:13])[NH:9][C:8]3[CH:14]=[CH:15][C:5]([CH3:4])=[CH:6][C:7]=3[S:12]2)=[CH:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 10256Indole-3-CarboxaldehydeHCID 6891047-Methyl-1,4-benzothiazin-3-oneHCID 10942334Sodium Methoxide

Product 1

HCID 57198983HCID 57198983, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Sodium methoxide (0.28 g, 5.2 mmol) was added in one portion to a solution of 7-methyl-2H-1,4-benzothiazin-3(4H)-one (0.72 g, 4.0 mmol) and indole-3-carboxaldehyde (0.88 g, 6.0 mmol) in dry DMF (4 mL). The mixture was heated for 48 h at 140° C., allowed to cool, then poured into water (60 ml). The precipitate was collected by filtration and washed with water. The precipitate was then refluxed with toluene (100 ml) and filtered hot to give a yellow solid which was purified by silica gel chromatography using a gradient of (100:1) to (100:20) toluene:ethanol as the mobile phase.

Workup

  1. temperatureto cool
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. temperatureThe precipitate was then refluxed with toluene (100 ml)
  5. filtrationfiltered hot
  6. customto give a yellow solid which
  7. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-ba552745cab7408da1ccc0fae45513e2
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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