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

HRID 1643897
Notes
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Reaction equation

HRID 1643897 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 benzyltrimethyl-ammonium 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-de4d98acd11943ed9efc99ecc693897e
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08119808B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes