Formamide → HCID 12021402, compound

HRID 2226205Notes

Reaction equation

HRID 2226205 reaction equation
[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:11][C:10]=2[C:9]([CH:21]=O)=[CH:8][CH:7]=1.[CH:24]([NH2:26])=[O:25].[OH-].[Na+]>C(O)=O>[CH3:1][N:2]([CH3:23])[CH2:3][CH2:4][NH:5][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:11][C:10]=2[C:9]([CH2:21][NH:26][CH:24]=[O:25])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 713FormamideHCID 14798Sodium HydroxideHCID 22915308HCID 22915308, compound

Product 1

HCID 12021402HCID 12021402, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 1-[[2-(dimethylamino)ethyl]amino]-9-oxothioxanthen-4-carboxaldehyde (4.75 g), formamide (66.5 mL) and formic acid (7.6 mL) was heated at 170° C. for 4 hours. The mixture was poured into ice water (250 mL), basified with 35% NaOH and extracted with chloroform. The organic layer was washed with water (2X), then brine (1X) and the solvent was dried over Na2SO4 and concentrated in vacuo to afford 6.2 g of N-[[1-[[2-(dimethylamino)ethyl]amino]-9-oxothioxanthen-4-yl]methyl]formamide.

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water (2X)
  3. dry with materialbrine (1X) and the solvent was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96d1598b97e443288adf2efd313cdff7
Source dataset
uspto-grants-1994_09
Patent number
US05346917

Reaction notes

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