Ammonia → HCID 22159509, compound

HRID 1089553Notes

Reaction equation

HRID 1089553 reaction equation
N.CC1C=CC(S([N:12]2[CH2:20][CH2:19][O:18][C:17]3[CH:21]=[CH:22][C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:16]=3[O:15][CH2:14][CH2:13]2)(=O)=O)=CC=1.[Na].[Cl-:31].[NH4+]>C(OCC)(=O)C.CO>[ClH:31].[O:18]1[C:17]2[CH:21]=[CH:22][C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:16]=2[O:15][CH2:14][CH2:13][NH:12][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 14856357HCID 14856357, compound

Product 1

HCID 22159509HCID 22159509, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To ammonia (50 mL) and CH3OH (9 mL) at -78° C. add 4-[(4-methylphenyl)sulfonyl]-9-[(methylsulfonyl)amino]-3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonine (8.5 g, 20 mmol) and sodium spheres (4.5 g, 0.20 mol). Monitor the progress of the reaction by thin-layer chromatography. Upon completion add ammonium chloride (11 g) and allow the reaction to warm to room temperature. Slurry the residue in ethyl acetate and remove the solid material by suction filtration through celite. Remove the solvent in vacuo. Dissolve the residue in CH3OH and add methanolic hydrochloric acid. Remove the solvent in vacuo and recrystallize from acetonitrile to obtain the title compound.

Workup

  1. customMonitor the progress of the reaction by thin-layer chromatography
  2. customthe reaction
  3. customremove the solid material
  4. filtrationby suction filtration through celite
  5. customRemove the solvent in vacuo
  6. dissolutionDissolve the residue in CH3OH
  7. additionadd methanolic hydrochloric acid
  8. customRemove the solvent in vacuo
  9. customrecrystallize from acetonitrile

Sources & evidence

ORD record
ord-4707bdd14a744fe483b07977f6f5ebe8
Source dataset
uspto-grants-1990_10
Patent number
US04966967

Reaction notes

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