Indole-3-Carboxaldehyde → HCID 69637135, compound

HRID 1825729Notes

Reaction equation

HRID 1825729 reaction equation
C[O-].[Na+].[OH: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>CN(C=O)C>[OH:4][C:5]1[CH:15]=[CH:14][C:8]2[NH:9][C:10](=[O:13])[C:11](=[CH:25][C:18]3[C:19]4[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=4)[NH:16][CH:17]=3)[S:12][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 10256Indole-3-CarboxaldehydeHCID 8200317-hydroxy-2H-1,4-benzothiazin-3(4H)-oneHCID 10942334Sodium Methoxide

Product 1

HCID 69637135HCID 69637135, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

Sodium methoxide (0.54 g, 10 mmol) was added in one portion to a solution of 7-hydroxy-2H-1,4-benzothiazin-3(4H)-one (0.91 g, 5 mmol) and indole-3-carboxaldehyde (1.09 g, 7.5 mmol) in dry DMF (5 ml). The mixture was heated at 140° C. for 48 h, allowed to cool and poured into ice water (60 ml). The solid was collected by filtration. The filtrate was acidified to pH=2 with 10% hydrochloric acid and the precipitated solid was collected by filtration. Both precipitates were put together, boiled with toluene and filtered hot to give a solid which was purified by silica gel chromatography using a gradient of (9:1) to (8:2) n-hexane/ethanol as the mobile phase.

Workup

  1. temperatureto cool
  2. filtrationThe solid was collected by filtration
  3. filtrationthe precipitated solid was collected by filtration
  4. filtrationfiltered hot
  5. customto give a solid which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-c097f5f292e646ce810a328a658dcc57
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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