HCID 178418361, compound → HCID 178456986, compound

HRID 1066149Notes

Reaction equation

HRID 1066149 reaction equation
[CH:1]([NH:4][C:5]1[NH:10][C:9]2[CH:11]=[CH:12][C:13]([N+:15]([O-])=O)=[CH:14][C:8]=2[S:7](=[O:19])(=[O:18])[N:6]=1)([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[NH2:15][C:13]1[CH:12]=[CH:11][C:9]2[NH:10][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[N:6][S:7](=[O:18])(=[O:19])[C:8]=2[CH:14]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178456988HCID 178456988, compound

Product 1

HCID 178456986HCID 178456986, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-isopropylamino-7-nitro-4H-1,2,4-benzothiadiazine 1,1-dioxide (0.6 g) in hot methanol (25 mL) was supplemented with 10% Pd/C (0.06 g) and submitted to hydrogen under pressure (4 bars) for 1 h at 40° C. The insoluble material was removed by filtration and the filtrate was concentrated to dryness by evaporation under reduced pressure. The residue of the crude title compound was recrystallized from methanol-water (yield: 0.45 g); m.p.: 278-283° C.; IR (KBr): 3455, 3363, 3216, 2972, 1618, 1575, 1510, 1298, 1255, 1174, 1146, 1113 cm−1; 1H-NMR (DMSO-d6, HMDS; d ppm): 1.10 (d, 6H, 2×CH3), 3.85 (m, 1H, NH—CH), 5.15 (bs, 2H, NH2), 6.50-6.95 (bm, 4H, 5-H+6-H+8-H+NH—CH), 9.75 (bs, 1H, NH).

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness by evaporation under reduced pressure
  3. customThe residue of the crude title compound was recrystallized from methanol-water (yield: 0.45 g)

Sources & evidence

ORD record
ord-3712af0fa70e423fb8112b1a0e6c24be
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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