Sodium Hydroxide → HCID 86671459, compound

HRID 1530504Notes

Reaction equation

HRID 1530504 reaction equation
Cl[S:2]([OH:5])(=[O:4])=[O:3].[CH:6]([N:9]1[C:13]([C:14]2[N:23]=[C:22]3[N:16]([CH2:17][CH2:18][O:19][C:20]4[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=43)[CH:15]=2)=[N:12][CH:11]=[N:10]1)([CH3:8])[CH3:7].[OH-].[Na+:29]>O>[CH:6]([N:9]1[C:13]([C:14]2[N:23]=[C:22]3[N:16]([CH2:17][CH2:18][O:19][C:20]4[CH:27]=[CH:26][C:25]([S:2]([O-:5])(=[O:4])=[O:3])=[CH:24][C:21]=43)[CH:15]=2)=[N:12][CH:11]=[N:10]1)([CH3:8])[CH3:7].[Na+:29]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acidHCID 68313479HCID 68313479, compound

Product 1

HCID 86671459HCID 86671459, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To chlorosulfonic acid (4 mL) at 0° C. was added 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene (400 mg, 1.35 mmol) portion wise and the resulting mixture stirred for 5 min then added drop wise to ice. NaOH (7.2 g) in H2O (20 mL) was added to the mixture and stirred for 1 h at RT then concentrated in vacuo. The resulting residue was purified by column chromatography (C18, gradient 0.5-1% MeOH in H2O) then extracted into hot MeOH. Upon cooling the mixture was filtered and the filtrate concentrated in vacuo affording Sodium 2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulene-9-sulfonate (1.32 g) contaminated with inorganic salts. LCMS: RT 2.14 min [M+H]+ 376.1

Workup

  1. additionthen added drop wise to ice
  2. stirringstirred for 1 h at RT
  3. concentrationthen concentrated in vacuo
  4. customThe resulting residue was purified by column chromatography (C18, gradient 0.5-1% MeOH in H2O)
  5. extractionthen extracted into hot MeOH
  6. temperatureUpon cooling the mixture
  7. filtrationwas filtered
  8. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-40bc3e40a5974c8ea9c61101ef42a337
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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