Hydrochloric Acid → 4-[[2-(1-Methylethyl)-3-indolizinyl]sulfonyl]phenol

HRID 1086300Notes

Reaction equation

HRID 1086300 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]([C:8]1[CH:9]=[C:10]2[N:15]([C:16]=1[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6].Cl>ClCCl.C(S)C>[CH:5]([C:8]1[CH:9]=[C:10]2[N:15]([C:16]=1[S:17]([C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)(=[O:19])=[O:18])[CH:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 14555118HCID 14555118, compound

Product 1

HCID 103358514-[[2-(1-Methylethyl)-3-indolizinyl]sulfonyl]phenol

Reagents, catalysts & solvents 2

HCID 6343EthanethiolSolventHCID 6344DichloromethaneSolvent2×

Procedure

6.7 g (0.050 mole) of aluminium chloride are suspended in 100 ml of dichloromethane and 25 ml of ethanethiol. This suspension is stirred and cooled to 0° C. while 2.5 g of 2-isopropyl 3-p-methoxyphenylsulfonyl indolizine in dichloromethane are added. The addition takes about 15 minutes. The reaction mixture is allowed to warm to room temperature and maintained there for 45 minutes. It is poured onto ice, then 5 ml of concentrated hydrochloric acid are added with stirring. The mixture is extracted with 2 fractions of ethyl ether and the ethereal extracts are pooled. They are washed with 3 fractions of 30 ml of a 10% aqueous solution of sodium bicarbonate and the aqueous phase is acidified.

Workup

  1. additionare added
  2. additionThe addition
  3. temperaturemaintained there for 45 minutes
  4. additionIt is poured onto ice
  5. stirringwith stirring
  6. extractionThe mixture is extracted with 2 fractions of ethyl ether
  7. washThey are washed with 3 fractions of 30 ml of a 10% aqueous solution of sodium bicarbonate

Sources & evidence

ORD record
ord-dadf82c642b3438f8c8e5e02b6292229
Source dataset
uspto-grants-1991_07
Patent number
US05028710

Reaction notes

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