Pyridine → HCID 18626144, compound

HRID 1859746Notes

Reaction equation

HRID 1859746 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12].[S:25](Cl)([C:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[C:33]([N:34]([CH3:36])[CH3:35])[C:32]=2[CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26]>O>[CH3:35][N:34]([CH3:36])[C:33]1[CH:37]=[CH:38][CH:39]=[C:40]2[C:32]=1[CH:31]=[CH:30][CH:29]=[C:28]2[S:25]([NH:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:12])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 84263-Amino-4-methoxybenzanilideHCID 11801Dansyl chloride

Product 1

HCID 18626144HCID 18626144, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyridine (5 mL) was added to a mixture of 3-amino-4-methoxy-N-phenyl-benzamide (0.73 g, 3.0 mmol) and dansyl chloride (0.81 g, 3.0 mmol) and stirred under an inert atmosphere at room temperature. After 20 hours, the mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×50 mL). The combined extracts were washed with water then saturated brine, then dried over MgSO4 and stripped of solvent under reduced pressure to afford the product (1.3 g); m.p. 231-232° C.

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined extracts were washed with water
  3. dry with materialsaturated brine, then dried over MgSO4

Sources & evidence

ORD record
ord-12cb6133ab1d4d0fa06b1f640a9ad5c3
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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