Pyridine → HCID 18626144, compound

HRID 1387589Notes

Reaction equation

HRID 1387589 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-6dfdd0b988904460a73aed53e9264c6b
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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