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

HRID 2198601Notes

Reaction equation

HRID 2198601 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.[CH3:19][S:20]([O:23][C:24]1[CH:25]=[CH:26][C:27]2[CH:31]=[C:30]([C:32]3[CH:37]=[CH:36][C:35]([O:38][S:39]([CH3:42])(=[O:41])=[O:40])=[CH:34][CH:33]=3)[S:29][C:28]=2[CH:43]=1)(=[O:22])=[O:21].[Cl-].[Al+3].[Cl-].[Cl-]>>[ClH:1].[CH3:19][S:20]([O:23][C:24]1[CH:25]=[CH:26][C:27]2[C:31]([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:30]([C:32]3[CH:33]=[CH:34][C:35]([O:38][S:39]([CH3:42])(=[O:40])=[O:41])=[CH:36][CH:37]=3)[S:29][C:28]=2[CH:43]=1)(=[O:21])=[O:22]

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 131748684-(2-Pyrrolidin-1-ylethoxy)benzoic acid hydrochlorideHCID 132860414-(6-(Methylsulfonyloxy)benzo(b)thiophen-2-yl)phenyl methanesulfonate

Product 1

HCID 1317128666-Methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

Procedure

The acid chloride of 20.4 g. of 4-(2-pyrrolidinoethoxy)benzoic acid, hydrochloride was prepared as described in Example 1, and was used to acylate 20 g. of 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene as described in Example 1, except that the amount of aluminum chloride was 60 g., of which 30 g. was added initially, and the rest was added in 10 g. portions at 15 minute intervals. The reaction mixture was stirred for 16 hours, and was worked up as described in Example 1 to obtain an oil, which was crystallized from denatured ethanol to obtain 27.5 g. of purified product, m.p. 196°-199°. A 4 g. sample was purified further by chromatography to obtain an analytical sample, m.p. 207°-207.5°.

Workup

  1. additionwas added initially
  2. additionthe rest was added in 10 g
  3. customto obtain an oil, which
  4. customwas crystallized from denatured ethanol
  5. customto obtain 27.5 g
  6. customsample was purified further by chromatography
  7. customto obtain an analytical sample, m.p. 207°-207.5°

Sources & evidence

ORD record
ord-ba77ff429af648c8824f99bd53e26cb2
Source dataset
uspto-grants-1982_11
Patent number
US04358593

Reaction notes

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