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

HRID 2198603Notes

Reaction equation

HRID 2198603 reaction equation
[ClH:1].[CH:2]([N:5]([CH:18]([CH3:20])[CH3:19])[CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)([CH3:4])[CH3:3].[CH3:21][S:22]([O:25][C:26]1[CH:27]=[CH:28][C:29]2[CH:33]=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([O:40][S:41]([CH3:44])(=[O:43])=[O:42])=[CH:36][CH:35]=3)[S:31][C:30]=2[CH:45]=1)(=[O:24])=[O:23].[Cl-].[Al+3].[Cl-].[Cl-]>C(O)C>[ClH:1].[CH:18]([N:5]([CH:2]([CH3:3])[CH3:4])[CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([C:33]2[C:29]3[CH:28]=[CH:27][C:26]([O:25][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:45][C:30]=3[S:31][C:32]=2[C:34]2[CH:35]=[CH:36][C:37]([O:40][S:41]([CH3:44])(=[O:42])=[O:43])=[CH:38][CH:39]=2)=[O:15])=[CH:16][CH:17]=1)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 132860414-(6-(Methylsulfonyloxy)benzo(b)thiophen-2-yl)phenyl methanesulfonateHCID 666256874-(2-Diisopropylaminoethoxy)benzoic acid hydrochloride

Product 1

HCID 1317128683-[4-(2-Diisopropylaminoethoxy)benzoyl]-6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene, hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 7.6 g. portion of 4-(2-diisopropylaminoethoxy)benzoic acid, hydrochloride, was converted to the acid chloride as described in Example 1 above, and was used to acylate 5 g. of 6-methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)benzo[b]thiophene in the presence of 20 g. of aluminum chloride. Work up according to Example 4 gave 7.4 g. of crystalline product after trituration of the isolated oil with denatured ethanol. The product was recrystallized from denatured ethanol to obtain 6.5 g. of purified product, and a 1.5 g. portion was further purified by chromatography over silica gel, eluting with 1:3 methanol:chloroform to obtain 1.15 g. of analytical sample, m.p. 198°-201°.

Workup

  1. customgave 7.4 g
  2. customThe product was recrystallized from denatured ethanol
  3. customto obtain 6.5 g
  4. customportion was further purified by chromatography over silica gel
  5. washeluting with 1:3 methanol
  6. customchloroform to obtain 1.15 g

Sources & evidence

ORD record
ord-881a8cf9edce4a779dcd1d31678b510d
Source dataset
uspto-grants-1982_11
Patent number
US04358593

Reaction notes

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