4-Toluenesulfonyl chloride → HCID 16739230, compound

HRID 415508Notes

Reaction equation

HRID 415508 reaction equation
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:14]3[O:15][CH2:16][CH2:17][CH2:18][C:13]3=[N:12][C:4]=1[CH:5]=[N+:6]2[O-].[NH4+:19].[OH-].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>ClCCl>[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[C:3]1[N:14]3[O:15][CH2:16][CH2:17][CH2:18][C:13]3=[N:12][C:4]=1[C:5]([NH2:19])=[N:6]2

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 66619891HCID 66619891, compound

Product 1

HCID 16739230HCID 16739230, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c]quinoline 5-oxide (0.364 g, 1.51 mmol) in 10 mL of dichloromethane was treated with 7 mL of concentrated aqueous NH4OH solution. The mixture was stirred rapidly and then p-toluenesulfonyl chloride (0.34 g, 1.78 mmol) was carefully added. Rapid stirring was continued for 2 hours. The reaction mixture was then diluted with more dichloromethane, washed successively with dilute aqueous K2CO3, H2O, and brine, dried over Na2SO4, and concentrated under reduced pressure. The solid was dissolved in hot CH3CN. The resulting crystals were filtered off and dried to give 0.0578 g of 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c]quinolin-6-amine as a tan solid, dec. 229-234° C. MS (APCI) m/z 241 (M+H)+; Anal. calcd for C13H12N4O: C, 64.99; H, 5.03; N, 23.32. Found: C, 64.81; H, 4.74; N, 23.44.

Workup

  1. stirringRapid stirring
  2. washwashed successively with dilute aqueous K2CO3, H2O, and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe solid was dissolved in hot CH3CN
  6. filtrationThe resulting crystals were filtered off
  7. customdried

Sources & evidence

ORD record
ord-66650e6f93da43358b989a83a3c739a2
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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