Sodium Bicarbonate → 12-Chloro-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-9-ylamine

HRID 513773Notes

Reaction equation

HRID 513773 reaction equation
C([NH:8][C:9]1[CH:26]=[C:25]2[C:12]([S:13](=[O:29])(=[O:28])[NH:14][C:15]3[C:24]2=[CH:23][C:22]([Cl:27])=[C:21]2[C:16]=3[N:17]=[CH:18][CH:19]=[CH:20]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])(O)=O.[Na+]>Br>[Cl:27][C:22]1[CH:23]=[C:24]2[C:15](=[C:16]3[C:21]=1[CH:20]=[CH:19][CH:18]=[N:17]3)[NH:14][S:13](=[O:28])(=[O:29])[C:12]1[C:25]2=[CH:26][C:9]([NH2:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68183316Benzyl-(12-chloro-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-9-yl)-amine

Product 1

HCID 6819028412-Chloro-6,6-dioxo-5,6-dihydro-6lambda*6*-thia-4,5-diaza-chrysen-9-ylamineYield 77%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of benzyl-(12-chloro-6,6-dioxo-5,6-dihydro-6λ*6*-thia-4,5-diaza-chrysen-9-yl)-amine 513 (218 mg, 0.52 mmol) in 48% aq. HBr (5 ml) was heated at 100° C. in a sealed tube for 3 h. After cooling, the mixture was neutralized with sat. NaHCO3 solution and the aqueous phase was extracted with EtOAc. The organic phase was washed with water, brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (50 mg, 77%).

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous phase was extracted with EtOAc
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography with DCM as the eluent

Sources & evidence

ORD record
ord-c25b1f9893444ecf92774f3f2429ff50
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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