Sulfuryl chloride → 9-chlorosulfonyl-5,6-dihydro-5-oxo-11H-indeno[1,2-c] Isoquinoline

HRID 2306568Notes

Reaction equation

HRID 2306568 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:4]=2[NH:3]1.[Cl:19][S:20](Cl)(=[O:22])=[O:21]>>[Cl:19][S:20]([C:15]1[CH:16]=[CH:17][C:18]2[C:4]3[NH:3][C:2](=[O:1])[C:11]4[C:6]([C:5]=3[CH2:12][C:13]=2[CH:14]=1)=[CH:7][CH:8]=[CH:9][CH:10]=4)(=[O:22])=[O:21]

Participants

3

Reactant 2

HCID 24648Sulfuryl chlorideHCID 101053885,6-dihydro-5-oxo-11H-indeno [1,2-c]isoquinoline

Product 1

HCID 112328219-chlorosulfonyl-5,6-dihydro-5-oxo-11H-indeno[1,2-c] IsoquinolineYield 92.2%

Procedure

Compound 6 (40 g, 0.17 mol) was added in small portions to chlorosulfonyl chloride (112 mL, 1.71 mol) at 0°C. and the reaction mixture was allowed to warm to room temperature and stir for 2 h. The reaction mixture was slowly poured on ice and the resulting yellow solid was filtered, washed thoroughly with water and EtOAc and dried in vacuo to provide the above-titled product 7 (52 g, 92%). 1H NMR (DMSO-D6): δ 3.91 (s, 2H), 7.43-7.48 (m, 1H), 7.60 (d, J=7.2 Hz, 1H), 7.74-7.76 (m, 2H), 7.79 (s, 1H), 7.90 (d, J=7.5 Hz, 1H), 8.23 (d, J=7.8 Hz, 1H), Anal. Calcd for C16H12ClNO4S: C, 54.94; H, 3.46; N, 4.00. Found C, 55.28; H, 3.43, N, 3.68, Karl-Fisher, 2.95.

Workup

  1. additionThe reaction mixture was slowly poured on ice
  2. filtrationthe resulting yellow solid was filtered
  3. washwashed thoroughly with water and EtOAc
  4. customdried in vacuo

Sources & evidence

ORD record
ord-d3263d77439b471dbcd1dca5d37d20ff
Source dataset
uspto-grants-2004_12
Patent number
US06828319B2

Reaction notes

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