Ammonia → 5-(4-Chlorophenyl)4-(2,4-dichlorophenyl)thiazole-2-carboxamide

HRID 1392372Notes

Reaction equation

HRID 1392372 reaction equation
[NH3:1].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14](OCC)=[O:15])=[N:11][C:10]=2[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])=[CH:5][CH:4]=1.[Na]>CO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C:14]([NH2:1])=[O:15])=[N:11][C:10]=2[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[Cl:26])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 10001752HCID 10001752, compound

Product 1

HCID 692892035-(4-Chlorophenyl)4-(2,4-dichlorophenyl)thiazole-2-carboxamideYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Part A: Gaseous NH3 is led through a stirred solution of ethyl 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxylate (1.65 gram, 4.0 mmol) in methanol (25 mL) at room temperature. A small piece of sodium metal is added. After stirring the resulting mixture for three hours the precipitate is collected by filtration, washed with a small portion of methanol and dried to give 5-(4-chlorophenyl)-4-(2,4-dichlorophenyl)thiazole-2-carboxamide (1.16 gram, 76% yield), melting point 195-198° C. 1H-NMR (200 MHz, CDCl3): δ 7.48 (br s, 1H), 7.22-7.35 (m, 4H), 7.05-7.20 (m, 3H) 5.55-5.65 (M, 1H).

Workup

  1. filtrationis collected by filtration
  2. washwashed with a small portion of methanol
  3. customdried

Sources & evidence

ORD record
ord-687cfac2b7ba46af97562190d0f8d4cd
Source dataset
uspto-grants-2008_03
Patent number
US07342032B2

Reaction notes

Loading…