Dithiooxamide → 2,5-Bis(3-tetradecoxycarbonyl-2-thienyl)-thiazolo[5,4-d]thiazole

HRID 523440Notes

Reaction equation

HRID 523440 reaction equation
[CH2:1]([O:15][C:16]([C:18]1[CH:22]=[CH:21][S:20][C:19]=1[CH:23]=O)=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[NH2:25][C:26]([C:28]([NH2:30])=[S:29])=[S:27]>>[CH2:1]([O:15][C:16]([C:18]1[CH:22]=[CH:21][S:20][C:19]=1[C:23]1[S:27][C:26]2[N:25]=[C:23]([C:19]3[S:20][CH:21]=[CH:22][C:18]=3[C:16]([O:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:17])[S:29][C:28]=2[N:30]=1)=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 2777982DithiooxamideHCID 86717684Tetradecyl-2-formylthiophene-3-carboxylate

Product 1

HCID 672935452,5-Bis(3-tetradecoxycarbonyl-2-thienyl)-thiazolo[5,4-d]thiazole

Conditions

Temperature
200 °C

Procedure

To a 25 mL flask were added 0.978 g (2.8 mmol) of tetradecyl-2-formylthiophene-3-carboxylate and 110 mg (0.9 mmol) of dithiooxamide. This mixture was heated to 200° C. for 2 hours. The resulting mixture was purified by column chromatography using a mixture of hexane and dichloromethane to give the desired compound. The NMR data were obtained and were consistent with those of the desired compound.

Workup

  1. customThe resulting mixture was purified by column chromatography
  2. additiona mixture of hexane and dichloromethane

Sources & evidence

ORD record
ord-2c570901f56a42438a3ee8151bf3eb2f
Source dataset
uspto-grants-2016_05
Patent number
US09337358B2

Reaction notes

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