Trimethyltin chloride → HCID 86717686, compound

HRID 523442Notes

Reaction equation

HRID 523442 reaction equation
[Cl:1][C:2]1[C:3]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])=[C:4]([C:7]2[S:8][C:9]3[N:10]=[C:11]([C:15]4[S:16][CH:17]=[C:18]([Cl:34])[C:19]=4[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[S:12][C:13]=3[N:14]=2)[S:5][CH:6]=1.C([Li])CCC.[CH3:54][Sn:55](Cl)([CH3:57])[CH3:56]>C(OCC)C>[CH3:54][Sn:55]([CH3:57])([CH3:56])[C:6]1[S:5][C:4]([C:7]2[S:8][C:9]3[N:10]=[C:11]([C:15]4[S:16][C:17]([Sn:55]([CH3:57])([CH3:56])[CH3:54])=[C:18]([Cl:34])[C:19]=4[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[S:12][C:13]=3[N:14]=2)=[C:3]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 67293669HCID 67293669, compoundHCID 178418339Butyllithium

Product 1

HCID 86717686HCID 86717686, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a 100 mL Schlenk flask was added 250 mg (0.32 mmol) of 2,5-bis(4-chloro-3-tetradecyl-2-thienyl)-thiazolo[5,4-d]thiazole. The flask was evacuated and refilled with argon three times. After 35 mL of dry THF was added to the flask, the flask was cooled to −78° C. n-Butyl lithium (0.96 mmol) was then added dropwise to the solution. After stirring at −78° C. for 1 hour, 1.1 mL of an 1.0 M solution of trimethyltin chloride was syringed into the reaction mixture. After the solution was allowed to warm up to room temperature, 100 mL of diethyl ether was added to the solution. The solution was washed three times with 100 mL of water and then the organic layer was dried MgSO4. The solvent was removed in vacuo and the desired compound, i.e., 2,5-bis(5-trimethylstannyl-4-chloro-3-tetradecyl-2-thienyl)-thiazolo[5,4-d]thiazole, was isolated in quantitative yield. The NMR data were obtained and were consistent with those of the desired compound.

Workup

  1. customThe flask was evacuated
  2. additionrefilled with argon three times
  3. additionAfter 35 mL of dry THF was added to the flask
  4. additionwas then added dropwise to the solution
  5. temperatureto warm up to room temperature
  6. washThe solution was washed three times with 100 mL of water
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ca18ea31133747178fae36ea59b855ae
Source dataset
uspto-grants-2016_05
Patent number
US09337358B2

Reaction notes

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