Acetic Acid → N-(8-chloro-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzene-sulfonamide

HRID 1363116Notes

Reaction equation

HRID 1363116 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][C@@H:7]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6]2)#[N:2].C(O)(=O)C.C1COCC1.I([Cl:35])(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.I(Cl)(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1>C(Cl)Cl>[Cl:35][C:11]1[CH:12]=[C:3]([C:1]#[N:2])[CH:4]=[C:5]2[C:10]=1[NH:9][CH2:8][CH:7]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 57347110Benyltrimethylammonium tetrachloroiodateHCID 66757946(S)-N-(6-Cyano-1,2,3,4-tetrahydro-quinolin-3-yl)-benzenesulfonamide

Product 1

HCID 66757150N-(8-chloro-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzene-sulfonamideYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of racemate 1G (313.4 mg, 1 mmol) in a mixed solvent of acetic acid (3 mL), THF (3 mL) and CH2Cl2 (3 mL) at RT was added benzyltrimethylammonium tetrachloroiodate (419 mg, 1 mmol). After addition, the mixture was stirred at RT for 30 min to become a clear yellow solution which was concentrated in vacuo. The residue was triturated with CH2Cl2 and H2O and the resultant solid filtered and washed with CH2Cl2 and H2O, dried in vacuo to give the title compound as an off-white solid (204 mg, 59%).

Workup

  1. additionAfter addition
  2. concentrationwas concentrated in vacuo
  3. customThe residue was triturated with CH2Cl2 and H2O
  4. filtrationthe resultant solid filtered
  5. washwashed with CH2Cl2 and H2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3d9f230832c54d0392d9492eaeca2ac4
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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