Glycine → HCID 67005864, compound

HRID 1513846Notes

Reaction equation

HRID 1513846 reaction equation
[CH2:1]([C:22]1[C:26]2[S:27][C:28]3[C:32]4[S:33][C:34](C(O)=O)=[C:35]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:31]=4[S:30][C:29]=3[C:25]=2[S:24][C:23]=1C(O)=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].NCC(O)=O>COCCOCCOCCOCCOC>[CH2:1]([C:22]1[C:26]2[S:27][C:28]3[C:32]4[S:33][CH:34]=[C:35]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[C:31]=4[S:30][C:29]=3[C:25]=2[S:24][CH:23]=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][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 750GlycineHCID 86659544HCID 86659544, compound2×

Product 1

HCID 67005864HCID 67005864, compound

Reagents, catalysts & solvents 1

HCID 8925TetraglymeSolvent

Conditions

Temperature
240 °C

Procedure

Decarboxylation (Step D) A mixture of the 3,7-diheneicosyl thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene-2,6-dicarboxylic acid (1.0 mmol) product of Example 11, Cu2O (0.10 mmol), and glycine (0.16 mmol) in tetraethyleneglycol dimethylether is heated to about 240° C. in a flask fitted with an outlet bubbler to monitor gas evolution. As the decarboxylation proceeds the evolved gas is periodically monitored. After about 1.5 hr no further gas is observed to evolve and after 2 hr total the reaction is terminated. The hot reaction mixture is filtered quickly to remove the copper oxide and other solid residue. The filtered solution is then cooled to RT, to afford a pale yellow precipitate. This is filtered from the solution and subsequently recrystallized hot to cold from toluene to give the desired product, 3,7-diheneicosylthieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene (DC21FT4) 1H NMR (CD2Cl2) 0.91 (6H, t, J=6.8 Hz), 1.15-1.50 (76H, m), 1.74-1.90 (4H, m), 2.78 (4H, m), and 7.02 (2H, s).

Workup

  1. customfitted with an outlet bubbler
  2. waitto evolve and after 2 hr
  3. customis terminated
  4. filtrationThe hot reaction mixture is filtered quickly
  5. customto remove the copper oxide and other solid residue
  6. temperatureThe filtered solution is then cooled to RT
  7. customto afford a pale yellow precipitate
  8. filtrationThis is filtered from the solution

Sources & evidence

ORD record
ord-ddf7a6323f124443b24abe7c4649e922
Source dataset
uspto-grants-2012_07
Patent number
US08217183B2

Reaction notes

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