Formamide → HCID 12021402, compound

HRID 1769179Notes

Reaction equation

HRID 1769179 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 (2×), then brine (1×) 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 (2×)
  3. dry with materialbrine (1×) and the solvent was dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-277e9ff555d44f988eb9d9286b774288
Source dataset
uspto-grants-1995_01
Patent number
US05380749

Reaction notes

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