Isopropyl-methyl-(6-nitro-benzothiazol-2-yl)-amine → N2-Isopropyl-N2-methyl-benzothiazole-2,6-diamine

HRID 1174911Notes

Reaction equation

HRID 1174911 reaction equation
[CH:1]([N:4]([CH3:17])[C:5]1[S:6][C:7]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:3])[CH3:2].[H][H]>[Pd].CCO.C1COCC1>[CH:1]([N:4]([CH3:17])[C:5]1[S:6][C:7]2[CH:13]=[C:12]([NH2:14])[CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 57771678Isopropyl-methyl-(6-nitro-benzothiazol-2-yl)-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 57771707N2-Isopropyl-N2-methyl-benzothiazole-2,6-diamineYield 90%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Combine isopropyl-methyl-(6-nitro-benzothiazol-2-yl)-amine (1.32 g, 5.25 mmol) and 5% palladium on carbon (3.00 g) in EtOH (50 mL) and THF (25 mL). Shake on a Parr shaker at 60 psi hydrogen at room temperature for 7 h. Filter with filter paper, washing with EtOH (20 mL), and concentrate in vacuo to afford the title compound (1.04 g, 90%). 1H NMR (400 MHz, CDCl3): δ 7.36 (d, 1H, J=8.4 Hz), 6.93 (d, 1H, J=2.2 Hz), 6.67 (dd, 1H, J=8.6, 2.4 Hz), 4.31 (m, 1H), 3.62 (s, 2H), 2.99 (s, 3H), 1.25 (d, 6H, J=6.6 Hz).

Workup

  1. filtrationFilter
  2. filtrationwith filter paper
  3. washwashing with EtOH (20 mL)
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-cbeeeea12068431c8273b3ccc30889a6
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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