4-Methyl-3-nitrobenzoyl chloride → 5-(4-Methyl-3-nitrobenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

HRID 512529

Reaction equation

HRID 512529 reaction equation
[NH2:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[N:4][C:3]=1[C:18]([NH2:20])=[O:19].[CH3:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][C:23]=1[N+:31]([O-:33])=[O:32]>N1C=CC=CC=1>[CH3:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:1][C:2]2[S:6][C:5]([NH:7][C:8]3[CH:17]=[CH:16][C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH:9]=3)=[N:4][C:3]=2[C:18]([NH2:20])=[O:19])=[O:27])=[CH:24][C:23]=1[N+:31]([O-:33])=[O:32]

Participants

4

Reactant 2

HCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 867033695-Amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

Product 1

HCID 867033715-(4-Methyl-3-nitrobenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamideYield 66%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

To a mixture of 5-amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide (0.2 g, 0.70 mmol) in pyridine (5 mL) was added a solution of 4-methyl-3-nitrobenzoyl chloride in pyridine (3 mL) at 0° C. under nitrogen atmosphere. The mixture was allowed to warm up to rt, and stirred for 16 hrs at rt. The solvent was evaporated, and the crude residue was suspended into EtOAc (20 mL). The resulting solids were collected by filtration and washed with MeOH (2×5 mL) to give 0.21 g (66% yield) of the titled compound.

Workup

  1. customThe solvent was evaporated
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with MeOH (2×5 mL)

Sources & evidence

ORD record
ord-85ebdae6dd3244adadaa17d15c588fcb
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Linked notes

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