Pyridine → 4-n-Pentylphenyl 5-n-pentyl-thieno[3,2-b]thiophene-2-carboxylate

HRID 980778Notes

Reaction equation

HRID 980778 reaction equation
[CH2:1]([C:6]1[S:13][C:12]2[CH:11]=[C:10]([C:14](Cl)=[O:15])[S:9][C:8]=2[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:17]([C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[CH2:18][CH2:19][CH2:20][CH3:21].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH2:1]([C:6]1[S:13][C:12]2[CH:11]=[C:10]([C:14]([O:28][C:25]3[CH:24]=[CH:23][C:22]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:27][CH:26]=3)=[O:15])[S:9][C:8]=2[CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 269754-PentylphenolHCID 566335225-n-Pentyl-thieno[3,2-b]thiophene-2-carboxylic acid chloride

Product 1

HCID 202204564-n-Pentylphenyl 5-n-pentyl-thieno[3,2-b]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3.5 g of 5-n-pentyl-thieno[3,2-b]thiophene-2-carboxylic acid chloride [obtainable by reacting 5-n-pentylthieno[3,2-b]thiophene-5-carboxylic acid (m.p. 156°, c.p. 196°) with thionyl chloride] in 20 ml of toluene are added dropwise to a mixture of 2.25 g of 4-n-pentylphenol, 1.08 g of pyridine and 30 ml of toluene, the mixture is heated to the boil for 2 hours and allowed to cool, the pyridine hydrochloride is filtered off, and the mixture is worked up in the usual manner. 4-n-Pentylphenyl 5-n-pentyl-thieno[3,2-b]thiophene-2-carboxylate of melting point 58° and clear point 93° is obtained.

Workup

  1. temperaturethe mixture is heated to the boil for 2 hours
  2. temperatureto cool
  3. filtrationthe pyridine hydrochloride is filtered off

Sources & evidence

ORD record
ord-0ab4f1dadaa140caa50d46a4b95cd1a8
Source dataset
uspto-grants-1987_01
Patent number
US04639328

Reaction notes

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