Ammonia → HCID 117728272, compound

HRID 1772676Notes

Reaction equation

HRID 1772676 reaction equation
N.[Br:2][C:3]1[CH:15]=[CH:14][C:6]2[NH:7][C:8](=[O:13])[NH:9][S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[CH3:16]I.O>CO.CN(C=O)C>[Br:2][C:3]1[CH:15]=[CH:14][C:6]2[NH:7][C:8](=[O:13])[N:9]([CH3:16])[S:10](=[O:11])(=[O:12])[C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 6328Methyl iodideHCID 101075322H-1,2,4-Benzothiadiazin-3(4H)-one, 7-bromo-, 1,1-dioxide

Product 1

HCID 117728272HCID 117728272, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Gaseous ammonia was passed through a suspension of 7-bromo-2H-benzo[e][1,2,4]thiadiazin-3(4H)-one 1,1-dioxide (760 mg, 2.7 mmol) in MeOH (8 mL) until a clear solution was obtained. The solvent was then evaporated and the residue was slurried with MeOH (5 mL) and filtered. The solid obtained was dissolved in DMF (5 mL) and treated with MeI (169 μL, 2.75 mmol). The reaction mixture was stirred at rt for 18 h, poured into water (20 mL) and extracted with EtOAc (3×50 mL). The combined EtOAc layer was dried over Na2SO4, filtered, and concentrated to obtain compound 42a. 1H-NMR (400 MHz, CD3OD) δ (ppm): 7.86 (d, J=2.0 Hz, 1H), 7.60 (dd, J=8.7, 2.1 Hz, 1H), 7.00 (d, J=8.6 Hz, 1H), 3.26 (s, 3H).

Workup

  1. customwas obtained
  2. customThe solvent was then evaporated
  3. filtrationfiltered
  4. customThe solid obtained
  5. extractionextracted with EtOAc (3×50 mL)
  6. dry with materialThe combined EtOAc layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0349ffcf37e94ccfa4feb293d3094eed
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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