Hydrochloric Acid → HCID 19085567, compound

HRID 962763Notes

Reaction equation

HRID 962763 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[O:18][CH2:19][CH2:20][CH2:21][Cl:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C([Cl:26])=O.[Cl-].[Al+3].[Cl-].[Cl-].[C:33]1([S:39]([N:42]2[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH:44]=[CH:43]2)(=[O:41])=[O:40])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.Cl>ClC(Cl)C>[Cl:22][CH2:21][CH2:20][CH2:19][O:18][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:13]([Cl:26])=[O:14].[OH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([C:44]2[C:45]3[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=3)[N:42]([S:39]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)(=[O:41])=[O:40])[CH:43]=2)=[O:15])=[CH:11][C:10]=1[O:18][CH2:19][CH2:20][CH2:21][Cl:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 3150171-(Phenylsulfonyl)-1H-indoleHCID 6451240Aluminum(III) ChlorideHCID 19085564HCID 19085564, compound

Product 2

HCID 19085567HCID 19085567, compoundHCID 19085585HCID 19085585, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

3-(3-Chloropropoxy)-4-benzyloxybenzoyl chloride, which was prepared using 4-benzyloxy-3-(3-chloropropoxy)benzoic acid (2.53 g) and oxalyl chloride (1 ml), was dissolved in dichloroethane (20 ml). Aluminum chloride (2.63 g) was added to the resultant solution while cooling on ice bath, stirred for 5 minutes at room temperature, and then cooled again on ice bath. 1-(Phenylsulfonyl)indole (1.69 g) in dichloroethane (10 ml) was added dropwise to the resultant mixture and stirred for 2.5 hours at room temperature. The reaction mixture was poured into 1N HCl and extracted with ethyl acetate. The resultant extract was sequentially washed with saturated sodium bicarbonate solution and brine and then dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1), obtaining 0.76 g of 3-[4-hydroxy-3-(3-chloropropoxy)benzoyl]-1-(phenylsulfonyl) indole as a yellow oily substance.

Workup

  1. temperaturewhile cooling on ice bath
  2. temperaturecooled again on ice bath
  3. stirringstirred for 2.5 hours at room temperature
  4. extractionextracted with ethyl acetate
  5. extractionThe resultant extract
  6. washwas sequentially washed with saturated sodium bicarbonate solution and brine
  7. customdried
  8. distillationThe solvent was distilled off
  9. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-e703061c645d43679835b9f1a482828e
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Reaction notes

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