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

HRID 1430422Notes

Reaction equation

HRID 1430422 reaction equation
CO.C(=O)([O-])[O-].[K+].[K+].[C:9]([NH:12][C:13]([NH:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[CH3:25])=[S:14])(=O)[CH3:10].BrCC([C:30]1[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=1)=O>O>[CH3:25][C:17]1[CH:18]=[CH:19][C:20]([N+:22]([O-:24])=[O:23])=[CH:21][C:16]=1[NH:15][C:13]1[S:14][CH:10]=[C:9]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[N:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 1514083-(2-Bromoacetyl)pyridineHCID 1546295N-[(2-methyl-5-nitrophenyl)carbamothioyl]acetamide

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
27.5 °C

Procedure

In a reactor, introduce methanol (1120 L), potassium carbonate (287 kg, 2076.70 mol) and 1-acetyl-3-(2-methyl-5-nitro-phenyl)-thiourea (67 kg, 264.53 mol). 2-bromo-1-pyridin-3-yl-ethanone (Int4) (52 kg, 259.96 mol) was then added and temperature maintained at 25-30° C. for 4 hours. Water (692 L) was added to the reaction mixture and precipitate filtered, washed with water and diisopropylether. The product was then dried in a tray drier at 45-50° C.

Workup

  1. filtrationfiltered
  2. washwashed with water and diisopropylether
  3. customThe product was then dried in a tray drier at 45-50° C.

Sources & evidence

ORD record
ord-c3886ede8b9f4b068d0ab028cd6efc08
Source dataset
uspto-grants-2015_01
Patent number
US08940894B2

Reaction notes

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