Dithiooxamide → HCID 86706804, compound

HRID 628234Notes

Reaction equation

HRID 628234 reaction equation
[CH2:1]([CH:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[CH:14]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[S:24]=[C:25]([C:27](=[S:29])[NH2:28])[NH2:26]>>[CH2:1]([CH:7]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:8][C:9]1[CH:13]=[CH:12][S:11][C:10]=1[C:14]1[S:24][C:25]2[N:26]=[C:14]([C:10]3[S:11][CH:12]=[CH:13][C:9]=3[CH2:8][CH:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[S:29][C:27]=2[N:28]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

3

Reactant 2

HCID 2777982DithiooxamideHCID 86706803HCID 86706803, compound

Product 1

HCID 86706804HCID 86706804, compound

Conditions

Temperature
200 °C

Procedure

Under a nitrogen atmosphere, 3-(2-hexyldecyl)-2thiophenaldehyde (3.00 g, 8.91 mmol) (A3) and rubeanic acid (375 mg, 2.97 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, 2,5-bis(3(2-hexyldecyl)thiophene-2-yl)thiazolo[5,4-d]thiazole (A4) was obtained as a yellow solid (630 mg, 28% yield). The product (A4) obtained was identified using a 1H-NMR method. 1H-NMR (400 MHZ, CDCl3, TMS) δ 7.34 (d, J=5.4 Hz, 1 H), 6.95 (d, j=5.4 Hz, 1 H), 2.93 (d, J=7.4 Hz, 2 H), 1.25 (m, 25 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-7075b135a17d4b019a393392b4cf30db
Source dataset
uspto-grants-2016_04
Patent number
US09312491B2

Reaction notes

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