3-(Aminosulfonyl)-4-chlorobenzoyl chloride → HCID 58107461, compound

HRID 873678Notes

Reaction equation

HRID 873678 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][C:7]=1[S:15](=[O:18])(=[O:17])[NH2:16].[CH2:19]([N:21]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]2[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=3[CH2:34][C:22]1=2)[CH3:20]>ClCCl>[Cl:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([C:31]2[CH:30]=[CH:29][C:28]3[C:23]4[CH2:24][CH2:25][C:26](=[O:27])[N:21]([CH2:19][CH3:20])[C:22]=4[CH2:34][C:33]=3[CH:32]=2)=[O:11])=[CH:8][C:7]=1[S:15]([NH2:16])(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 58107514HCID 58107514, compound

Product 1

HCID 58107461HCID 58107461, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under nitrogen, aluminum chloride (0.7 g, 4.9 mmol) is slurried in dichloromethane (15 mL) then 4-chloro-3-sulfamoyl-benzoyl chloride (287 mg, 1.13 mmol) is added and allowed to stir at ambient temperature for 30 minutes. Then 1-ethyl-1,3,4,9-tetrahydro-indeno[2,1-b]pyridin-2-one (240 mg, 1.13 mmol) is added in 4 mL dichloromethane. The reaction is allowed to stir at ambient temperature for 1.5 hours. The reaction mixture is poured over ice-water and extracted with dichloromethane, the organic layer is separated and concentrated to give crude title compound as a brown oil. Recrystallization from warm dichloromethane afforded the title compound as a yellow powder (125 mg, 26% yield). 1H NMR (MeOD) 1.26 (t, 2H, J=7.01 Hz), 2.76-2.83 (m, 4H), 3.6 (s, 2H), 3.77 (q, 2H, J=7.01), 5.19 (s, 2H), 7.19 (d, 1H, J=8.11 Hz), 7.68-7.73 (m, 2H), 7.86 (d, 1H, J=1.09), 7.94 (dd, 1H, J=2.19, 8.11 Hz), 8.46 (d, 1H, J=1.97 Hz), MS (m/z): 431 (M+1).

Workup

  1. stirringto stir at ambient temperature for 1.5 hours
  2. extractionextracted with dichloromethane
  3. customthe organic layer is separated
  4. concentrationconcentrated
  5. customto give crude title compound as a brown oil
  6. customRecrystallization
  7. temperaturefrom warm dichloromethane

Sources & evidence

ORD record
ord-bed3e05d165c48aa8737fbb9bf55bfb8
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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