HCID 12351492, compound → HCID 86699717, compound

HRID 1844100Notes

Reaction equation

HRID 1844100 reaction equation
[CH3:1][S:2][CH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:12]([O-])=O)[NH:5][C:4]1=[O:15]>C(O)C.C(O)(=O)C>[NH2:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:3]([S:2][CH3:1])[C:4](=[O:15])[NH:5]2

Participants

4

Reactant 1

HCID 12351492HCID 12351492, compound

Product 1

HCID 86699717HCID 86699717, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of compound D1 (1 g), stannous chloride dihydrate (5.03 g) in 36 mL of ethanol and acetic acid (EtOH:AcOH:5:1) was heated at 70° C. under argon. Reaction was monitored using TLC and terminated after 7 hrs on disappearance of the starting material. The reaction mixture was cooled, solvent evaporated to give a sticky solid, water added, then extracted with chloroform. Saturated sodium bicarbonate was added stepwise to water layer, extracted with chloroform. Organic layers were combined, washed with saturated sodium bicarbonate and brine solution, dried over MgSO4, filtered and concentrated to give crude product, which was washed with toluene to give the title compound D2. YD: 95.85%. 1H NMR (DMSO-d6) 400 MHz. δ: 1.888 (s, 3H) 4.303 (s, 1H), 5.121 (s, 2H), 6.050 (d, J=7.6 Hz, 1H), 6.250 (d, J=8.4, 1H), 6.889 (dd, J=7.6 & 8.0 Hz, 1H), 10.231 (s, 1H). MS (ESI): m/z 217.0 [M+Na]+.

Workup

  1. customReaction
  2. customterminated after 7 hrs on disappearance of the starting material
  3. temperatureThe reaction mixture was cooled
  4. customsolvent evaporated
  5. customto give a sticky solid, water
  6. additionadded
  7. extractionextracted with chloroform
  8. additionSaturated sodium bicarbonate was added stepwise to water layer
  9. extractionextracted with chloroform
  10. washwashed with saturated sodium bicarbonate and brine solution
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated
  14. customto give crude product, which
  15. washwas washed with toluene

Sources & evidence

ORD record
ord-3f0cfde23898414080030a75d72919f1
Source dataset
uspto-grants-2015_02
Patent number
US08946282B2

Reaction notes

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