Diazoxide → 1098065-76-9

HRID 2100340Notes

Reaction equation

HRID 2100340 reaction equation
[CH3:1][C:2]1[NH:13][C:12]2[CH:11]=[CH:10][C:9]([Cl:14])=[CH:8][C:7]=2[S:4](=[O:6])(=[O:5])[N:3]=1.[OH-].[OH:16][CH2:17][CH2:18][N+:19]([CH3:22])([CH3:21])[CH3:20]>C1COCC1>[CH3:1][C:2]1[N-:3][S:4](=[O:5])(=[O:6])[C:7]2[CH:8]=[C:9]([Cl:14])[CH:10]=[CH:11][C:12]=2[N:13]=1.[CH3:20][N+:19]([CH2:18][CH2:17][OH:16])([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 3019DiazoxideHCID 31255Choline, hydroxide2×

Product 1

HCID 250148111098065-76-9

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A 12-L reaction flash was charged with 2.0 kg diazoxide and 5.0-L THF with stirring and heating to 55° C. Choline hydroxide (45% solution in methanol, 2.32 L) was added dropwise to this reaction mixture over about 2.5 hr with stirring. The temperature was maintained at 60±5° C. After addition of choline hydroxide, stirring was continued for about 30 min. The reaction mixture was clarified by in-line 10 micron filtration upon transfer to a 22-L reaction flask pre-charged with 2-L pre-filtered THF, into which was added 10-L pre-filtered MTBE dropwise. This reaction mixture was transferred to another flask which was then charged with an additional 30-L pre-filtered MTBE dropwise, with adjustment of temperature to <5° C. and stirring for about 2 hr. Diazoxide choline salt was recovered by vacuum filtration to afford 2.724 kg (94%) diazoxide choline salt (99.8%, HPLC purity), confirmed by 1H NMR, IR, and UV/Visible analysis.

Workup

  1. stirringwith stirring
  2. temperatureThe temperature was maintained at 60±5° C
  3. stirringstirring
  4. filtrationThe reaction mixture was clarified by in-line 10 micron filtration upon transfer to a 22-L reaction flask
  5. additionpre-charged with 2-L
  6. filtrationpre-filtered THF
  7. additioninto which was added 10-L
  8. filtrationpre-filtered MTBE dropwise
  9. customThis reaction mixture was transferred to another flask
  10. additionwhich was then charged with an additional 30-L
  11. filtrationpre-filtered MTBE dropwise
  12. stirringwith adjustment of temperature to <5° C. and stirring for about 2 hr
  13. filtrationDiazoxide choline salt was recovered by vacuum filtration

Sources & evidence

ORD record
ord-b586164cea12441297cb8b53dad60f06
Source dataset
uspto-grants-2009_08
Patent number
US07572789B2

Reaction notes

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