Hydrochloric Acid → 1,4-Dihydro-6,7-dichloro-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-ylmethyl]quinoxalin-2,3-dione

HRID 1957115Notes

Reaction equation

HRID 1957115 reaction equation
[Cl:1][C:2]1[C:3]([CH2:17][N:18]2[C:22]3[CH:23]=[CH:24][C:25]([CH2:27][N:28]([CH3:30])[CH3:29])=[CH:26][C:21]=3[N:20]=[N:19]2)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13]C)[C:6]([O:15]C)=[N:5]2.Cl>O1CCOCC1>[Cl:1][C:2]1[C:3]([CH2:17][N:18]2[C:22]3[CH:23]=[CH:24][C:25]([CH2:27][N:28]([CH3:30])[CH3:29])=[CH:26][C:21]=3[N:20]=[N:19]2)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[C:6](=[O:15])[NH:5]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 543919756,7-dichloro-2,3-dimethoxy-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-ylmethyl]quinoxaline

Product 1

HCID 190688961,4-Dihydro-6,7-dichloro-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-ylmethyl]quinoxalin-2,3-dioneYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 6,7-dichloro-2,3-dimethoxy-5-[5-(N,N-dimethylaminomethyl)-1,2,3-benzotriazol-1-ylmethyl]quinoxaline (Preparation 24, 110 mg, 0.25 mmol), 2M hydrochloric acid (10 mL) and dioxane (10 mL) was heated at reflux for 5.5 hours. The mixture was concentrated under reduced pressure, diluted with acetone (10 mL) and filtered. The solid was dried under vacuum to give the title compound as an off-white solid (97 mg, 94%), mp 282° C. Found: C, 45.57; H, 4.00; N, 17.67. C18H16Cl2N6 O2. HCl.H2O requires C, 45.64; H, 4.04; N, 17.74%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 5.5 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. additiondiluted with acetone (10 mL)
  5. filtrationfiltered
  6. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-b0c66b9f8be8405bb337e333ed816dd8
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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