Dimethylformamide → HCID 86642820, compound

HRID 1667711Notes

Reaction equation

HRID 1667711 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:14]([NH2:16])=[O:15])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.F[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27].CN(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[Cl:13][C:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:6]=[C:2]([NH:1][C:18]3[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][C:19]=3[N+:26]([O-:28])=[O:27])[S:3][C:4]=2[C:14]([NH2:16])=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 5981294-Fluoro-3-nitrobenzaldehydeHCID 59375349HCID 59375349, compound

Product 1

HCID 86642820HCID 86642820, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 0.10 g (0.39 mmole) of 2-amino-4-(4-chloro-phenyl)-thiazole-5-carboxylic acid amide (V.18), 0.07 g (0.39 mmole) of 4-fluoro-3-nitrobenzaldehyde and 2 mL of dimethylformamide was added 0.19 g (0.59 mmole) of cesium carbonate. The mixture was heated at 120 degrees for 6 hours and then cooled. Water was then added and the suspension stirred at room temperature for one hour. The precipitate was collected by filtration, washed with water and dried under vacuum to give 0.16 g of 4-(4-chloro-phenyl)-2-(4-formyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide (VI.18a).

Workup

  1. temperatureThe mixture was heated at 120 degrees for 6 hours
  2. temperaturecooled
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-a0fc1145f83d41e7b08452daa6000ab3
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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