Formamide → SR271425

HRID 1769188Notes

Reaction equation

HRID 1769188 reaction equation
[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][NH:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH3:23])[CH:17]=3)[S:12][C:11]=2[C:10]([CH:24]=O)=[CH:9][CH:8]=1)[CH3:2].[CH:28]([NH2:30])=[O:29].[OH-].[Na+]>>[CH2:1]([N:3]([CH2:26][CH3:27])[CH2:4][CH2:5][NH:6][C:7]1[C:20]2[C:19](=[O:21])[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:22][CH3:23])[CH:17]=3)[S:12][C:11]=2[C:10]([CH2:24][NH:30][CH:28]=[O:29])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 3

HCID 713FormamideHCID 14798Sodium HydroxideHCID 13504755HCID 13504755, compound

Product 1

HCID 9909677SR271425

Conditions

Temperature
170 °C

Procedure

A mixture of 1-[[2-(diethylamino)ethyl]amino]-7-methoxy-9-oxothioxanthen-4-carboxaldehyde (3.6 g, 0. 0094 mol), formamide (48 mL) nd formic acid (6 mL) was heated to 170° C. under N2 for 8 hours. The mixture was poured into ice-water, basified with 35% NaOH and extracted with chloroform. The organic layer was separated, washed with water (2×), then brine and was dried over Na2SO4 and concentrated in vacuo to afford 3.88 g of N-[[1-[[2-(diethylamino) ethyl]amino]-7-methoxy-9-oxothioxanthen-4-yl]-methyl ]formamide.

Workup

  1. extractionextracted with chloroform
  2. customThe organic layer was separated
  3. washwashed with water (2×)
  4. dry with materialbrine and was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-13dc3179dd6a4c3cb8d1d9de3f723084
Source dataset
uspto-grants-1995_01
Patent number
US05380749

Reaction notes

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