Ammonium Chloride → HCID 18679742, compound

HRID 1633716Notes

Reaction equation

HRID 1633716 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([S:7]([N:10]([CH3:12])[CH3:11])(=[O:9])=[O:8])[CH:6]=1.C([Mg]Br)C.[CH3:17][O:18][C:19]1[C:20]([N+:30]([O-:32])=[O:31])=[C:21]2[C:26](=[CH:27][CH:28]=1)[C:25](=[O:29])[CH2:24][CH2:23][CH2:22]2.[Cl-].[NH4+]>ClCCl>[OH:29][C:25]1([C:2]2[N:3]=[CH:4][N:5]([S:7]([N:10]([CH3:12])[CH3:11])(=[O:9])=[O:8])[CH:6]=2)[C:26]2[C:21](=[C:20]([N+:30]([O-:32])=[O:31])[C:19]([O:18][CH3:17])=[CH:28][CH:27]=2)[CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2773390N,N-Dimethyl 4-iodo-1H-imidazole-1-sulfonamideHCID 130673376-Methoxy-5-nitro-1,2,3,4-tetrahydronaphthalen-1-oneHCID 178418443HCID 178418443, compound

Product 1

HCID 18679742HCID 18679742, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-iodo-N,N-dimethyl-1H-imidazole-1-sulfonamide (3.0 g, 10 mmol) (R. M. Turner, J. Org. Chem. (1991), 56, 5739-5740) in dichloromethane (40 mL) was treated with ethyl magnesium bromide (3.0M in diethyl ether, 3.3 mL) over 5 minutes, stirred for 30 minutes, treated with 6-methoxy-5-nitro-1-tetralone (2.6 g, 11.8 mmol), stirred for 16 hours, treated with ammonium chloride solution and extracted with dichloromethane. The extract was dried (MgSO4), filtered and concentrated to provide the desired compound.

Workup

  1. stirringstirred for 16 hours
  2. extractionextracted with dichloromethane
  3. dry with materialThe extract was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ef094213dff74786b4547236844aa51b
Source dataset
uspto-grants-2003_01
Patent number
US06503935B1

Reaction notes

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