Dithiooxamide → HCID 86706807, compound

HRID 628237Notes

Reaction equation

HRID 628237 reaction equation
[CH:1]([C:3]1[S:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH:10]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=O.[S:21]=[C:22]([C:24](=[S:26])[NH2:25])[NH2:23]>>[CH2:17]([CH:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][O:8][C:7]1[CH:6]=[CH:5][S:4][C:3]=1[C:1]1[S:21][C:22]2[N:23]=[C:1]([C:3]3[S:4][CH:5]=[CH:6][C:7]=3[O:8][CH2:9][CH:10]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[S:26][C:24]=2[N:25]=1)[CH2:18][CH2:19][CH3:20]

Participants

3

Reactant 2

HCID 2777982DithiooxamideHCID 86706806HCID 86706806, compound

Product 1

HCID 86706807HCID 86706807, compoundYield 29%

Conditions

Temperature
200 °C

Procedure

Under a nitrogen atmosphere, 2-formyl-3-(2-butyloctoxy)thiophene (7 g, 23.6 mmol) and rubeanic acid (1.42 g, 11.8 mmol) were added to a flask equipped with Dean-Stark, then heated to 200° C., and stirred for five hours. Then, the reaction mixture was extracted with chloroform, and an organic layer was washed with a saturated saline solution and water. The organic layer was dried with anhydrous magnesium sulfate, and, after filtration, the solvent was distilled off under reduced pressure. By separating and purifying the obtained reaction mixture by silica gel column chromatography in which a mixed solvent of hexane and chloroform was used as a mobile phase, a target substance was obtained as a yellow solid (29% yield). 1H-NMR (400 MHZ, CDCl3, TMS) δ 7.31 (d, J=5.6 Hz, 1 H), 6.88 (d, J=5.6 Hz, 1 H), 4.13 (d, J=4.8 Hz, 2 H), 1.25 (m, 17 H), 0.88 (m, 6 H)

Workup

  1. customequipped with Dean-Stark
  2. extractionThen, the reaction mixture was extracted with chloroform
  3. washan organic layer was washed with a saturated saline solution and water
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. filtrationafter filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customBy separating
  8. custompurifying
  9. customthe obtained reaction mixture by silica gel column chromatography in which a mixed solvent of hexane and chloroform

Sources & evidence

ORD record
ord-562fc6b5a0f74101a7970423a33d01e4
Source dataset
uspto-grants-2016_04
Patent number
US09312491B2

Reaction notes

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