N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)-1,3-thiazol-2-amine → HCID 44249598, compound

HRID 1430423Notes

Reaction equation

HRID 1430423 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:16]=1.[H][H]>[Ni].CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[N:16]=1

Participants

5

Reactant 2

HCID 44249597N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl)-1,3-thiazol-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 44249598HCID 44249598, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a reactor, a mixture of (2-methyl-5-nitro-phenyl)-(4-pyridin-3-yl-thiazol-2-yl)-amine (40 kg, 128.06 mol), Raney Nickel (2.7 kg, 46.00 mol) and methanol (600 L), was warmed to 40-45° C. and hydrogenated under hydrogen pressure (5 kg/cm2) for 2 hours. The reaction mixture was filtered and concentrated. Water was added to the residue under stirring. The product was then filtered and dried in a tray drier at 45-50° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. additionWater was added to the residue
  4. filtrationThe product was then filtered
  5. customdried in a tray drier at 45-50° C.

Sources & evidence

ORD record
ord-50916f1c69f34bbbaf25a960dd2ea7b0
Source dataset
uspto-grants-2015_01
Patent number
US08940894B2

Reaction notes

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