Carbon Dioxide → HCID 16103490, compound

HRID 646545Notes

Reaction equation

HRID 646545 reaction equation
[CH2:1]([C:11]1[C:15]2[S:16][C:17]3[C:21]4[S:22][C:23](C(O)=O)=[C:24]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:20]=4[S:19][C:18]=3[C:14]=2[S:13][C:12]=1C(O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C(=O)=O.CCCCCC>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH2:25]([C:24]1[C:20]2[S:19][C:18]3[C:14]4[S:13][CH:12]=[C:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[C:15]=4[S:16][C:17]=3[C:21]=2[S:22][CH:23]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 8058HexaneHCID 16103460HCID 16103460, compound

Product 1

HCID 16103490HCID 16103490, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
255 °C

Procedure

Compound 75 (13.5 g, 0.021 mol) was mixed with copper powder (0.9 g) in quinoline (80 mL), and the mixture was heated to 250-260° C. in a Woods-metal bath. When no further bubbles of carbon dioxide gas could be detected (about 2 hours), the mixture was allowed to cool to room temperature and hot hexane (400 mL) was added. This mixture was then repeated washed by HCl (2N, 4×50 mL). The hexane was partially removed by evaporation, and the resultant solid was collected by filtration and re-crystallized from hexane to afford compound 70 (7.0 g, 60.6% yield). M.p. 111.0-113.3° C. 1H NMR (C6D6) δ 6.53 (s, 2H), 2.51 (t, 4H), 1.64 (m, 4H), 1.27 (m, 28H), 0.89 (t, 6H). 13C NMR: 141.26, 136.42, 133.17, 132.04, 120.73, 32.31, 30.03, 29.96, 29.90, 29.79, 29.66, 29.04, 23.07, 14.28.

Workup

  1. custom(about 2 hours)
  2. temperatureto cool to room temperature
  3. washThis mixture was then repeated washed by HCl (2N, 4×50 mL)
  4. customThe hexane was partially removed by evaporation
  5. filtrationthe resultant solid was collected by filtration
  6. customre-crystallized from hexane

Sources & evidence

ORD record
ord-0394af8888cc4b39af9c411339dff524
Source dataset
uspto-grants-2010_04
Patent number
US07705108B2

Reaction notes

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