Aluminum(III) Chloride → 6-Benzoyloxy-2-(4-benzoyloxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

HRID 2198600Notes

Reaction equation

HRID 2198600 reaction equation
[ClH:1].[N:2]1([CH2:7][CH2:8][O:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[C:19]([O:27][C:28]1[CH:29]=[CH:30][C:31]2[CH:35]=[C:34]([C:36]3[CH:41]=[CH:40][C:39]([O:42][C:43](=[O:50])[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[CH:38][CH:37]=3)[S:33][C:32]=2[CH:51]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[ClH:1].[C:19]([O:27][C:28]1[CH:29]=[CH:30][C:31]2[C:35]([C:14](=[O:16])[C:13]3[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][N:2]4[CH2:3][CH2:4][CH2:5][CH2:6]4)=[CH:18][CH:17]=3)=[C:34]([C:36]3[CH:41]=[CH:40][C:39]([O:42][C:43](=[O:50])[C:44]4[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=4)=[CH:38][CH:37]=3)[S:33][C:32]=2[CH:51]=1)(=[O:26])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 99116044-(6-(Benzoyloxy)benzo[b]thiophen-2-yl)phenyl benzoateHCID 131748684-(2-Pyrrolidin-1-ylethoxy)benzoic acid hydrochloride

Product 1

HCID 1317128656-Benzoyloxy-2-(4-benzoyloxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

Procedure

An acid chloride was formed from 18.1 g. of 4-(2-pyrrolidinoethoxy)benzoic acid, hydrochloride, as described in Example 1. The acid chloride was used to acylate 20 g. of 6-benzoyloxy-2-(4-benzoyloxyphenyl)benzo[b]thiophene as described above in Example 1, using 53.2 g. of aluminum chloride. A sample of the impure product, a tan foam, was recrystallized from denatured ethanol to obtain an analytical sample, m.p. 218°-222°.

Workup

  1. customA sample of the impure product, a tan foam, was recrystallized from denatured ethanol
  2. customto obtain an analytical sample, m.p. 218°-222°

Sources & evidence

ORD record
ord-f84fc074755c4c86bd850b62b0c52afd
Source dataset
uspto-grants-1982_11
Patent number
US04358593

Reaction notes

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