Hydrochloric Acid → HCID 18675455, compound

HRID 2229761Notes

Reaction equation

HRID 2229761 reaction equation
[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[CH2:6]1)(=[O:4])=[O:3].[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(=S)=S.C(Cl)Cl.O>[CH3:1][S:2]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:26](=[O:27])[C:25]3[CH:29]=[CH:30][C:22]([Cl:21])=[CH:23][CH:24]=3)=[CH:11][CH:12]=2)[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=2)[CH2:6]1)(=[O:3])=[O:4]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 85014-Chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18675452HCID 18675452, compound

Product 1

HCID 18675455HCID 18675455, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 1-methylsulfonyl-3-(3-chlorophenyl)indoline (4.40 g, 14.3 mmol, see Preparation 5) and 4-chlorobenzoyl chloride (3.25 g, 18.6 mmol) in CS2 (25 mL) was added portionwise AlCl3 (7.62 g, 57.2 mmol) at about 0° C. A brown precipitate formed immediately. The mixture was stirred for about 2 hours. To the mixture was added slowly 100 mL of cold water containing 3 mL of concentrated HCl. The solution was diluted with DCM and the organic layer was separated and washed with 1N HCl aqueous solution (2 times), saturated NaHCO3 aqueous solution (2 times) and brine (2 times), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica, eluting with EtOAc/hexane 1:2. The title compound was obtained as a solid. Yield=3.90 g, 61%. Rf=0.24 (silica, EtOAc/hexane 1:2). MS (ES): 445.2; Calc. MW=445.4, 1H NMR (300 MHz, CDCl3) δ: 7.67-7.76 (m, 3H), 7.53-7.59 (m, 2H), 7.48 (s, 1H), 7.44 (s, 1H), 7.30-7.32 (m, 2H), 7.20 (m1H), 7.09-7.14 (m, 1H), 4.65 (t, 1H), 4.50 (t, 1H), 3.98 (dd, 1H), 3.02 (s, 3H).

Workup

  1. customA brown precipitate formed immediately
  2. customthe organic layer was separated
  3. washwashed with 1N HCl aqueous solution (2 times), saturated NaHCO3 aqueous solution (2 times) and brine (2 times)
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica
  8. washeluting with EtOAc/hexane 1:2

Sources & evidence

ORD record
ord-f8934bb8552b467da91cf5bb5f263752
Source dataset
uspto-grants-2002_07
Patent number
US06420555B1

Reaction notes

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