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

HRID 2198602Notes

Reaction equation

HRID 2198602 reaction equation
[ClH:1].[CH2:2]([N:4]([CH2:17][CH3:18])[CH2:5][CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1)[CH3:3].[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].[CH2:17]([N:4]([CH2:2][CH3:3])[CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([C:31]2[C:27]3[CH:26]=[CH:25][C:24]([O:23][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:43][C:28]=3[S:29][C:30]=2[C:32]2[CH:33]=[CH:34][C:35]([O:38][S:39]([CH3:42])(=[O:40])=[O:41])=[CH:36][CH:37]=2)=[O:14])=[CH:15][CH:16]=1)[CH3:18]

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 132860414-(6-(Methylsulfonyloxy)benzo(b)thiophen-2-yl)phenyl methanesulfonateHCID 429374924-[2-(Diethylamino)ethoxy]benzoic acid hydrochloride

Product 1

HCID 1317128673-[4-(2-Diethylaminoethoxy)benzoyl]-6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene, hydrochloride

Procedure

A 5.2 g. portion of 4-(2-diethylaminoethoxy)benzoic acid, hydrochloride, was converted to the acid chloride, and used to acylate 5 g. of 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene according to the process of Example 5. The amount of aluminum chloride was 15.1 g., and the reaction mixture was stirred for 1.5 hours after its addition. The mixture was worked up as described in Example 5 to obtain a yellow foam, which began to crystallize after standing for several days. It was triturated with denatured ethanol and recrystallized from denatured ethanol to obtain 6.5 g. of purified crystalline product, m.p. 172°-174°.

Workup

  1. additionafter its addition
  2. customto obtain a yellow foam, which
  3. customto crystallize
  4. waitafter standing for several days
  5. customIt was triturated with denatured ethanol
  6. customrecrystallized from denatured ethanol
  7. customto obtain 6.5 g

Sources & evidence

ORD record
ord-03f1abe4dd964f38af4cda8f582ecf2a
Source dataset
uspto-grants-1982_11
Patent number
US04358593

Reaction notes

Loading…