Sodium Bicarbonate → 2-Methyl-5,6-dihydro-4H-3-thia-1,6-diaza-benzo[e]azulene

HRID 220787Notes

Reaction equation

HRID 220787 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7](C(C3C=CC=CC=3)=O)[C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[N:11]=1.C([O-])(O)=O.[Na+]>Cl>[CH3:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][NH:7][C:8]3[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=3[C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 516892Sodium Bicarbonate2×HCID 23112323(2-Methyl-4,5-dihydro-3-thia-1,6-diaza-benzo[e]azulen-6-yl)-phenyl-methanone

Product 1

HCID 231123442-Methyl-5,6-dihydro-4H-3-thia-1,6-diaza-benzo[e]azuleneYield 76%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of (2-methyl-4,5-dihydro-3-thia-1,6-diaza-benzo[e]azulen-6-yl)-phenyl-methanone from Example E7.1 (0.42 g, 1.3 mmol) in 6M hydrochloric acid (45 ml) was heated at reflux for 16 h. The solution was cooled and treated with saturated NaHCO3 (aq) (10 ml). Additional solid NaHCO3 was added until the solution was basic. The mixture was extracted with dichloromethane and the organic extracts were dried and reduced in vacuo to yield the title compound as a yellow oil (0.21 g, 76%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. temperatureThe solution was cooled
  4. extractionThe mixture was extracted with dichloromethane
  5. customthe organic extracts were dried

Sources & evidence

ORD record
ord-fcb20fc5389b4e96ae1caa1b100418e7
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

Loading…