Water → 2-[(2Z)-5-Bromo-2-[(4-methylbenzene-1-sulfonyl)imino]pyridin-1(2H)-yl]acetamide

HRID 555983Notes

Reaction equation

HRID 555983 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4]/[C:5](=[N:8]/[S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])/[NH:6][CH:7]=1.CCN(C(C)C)C(C)C.Br[CH2:29][C:30]([NH2:32])=[O:31].O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4]/[C:5](=[N:8]/[S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])/[N:6]([CH2:29][C:30]([NH2:32])=[O:31])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 696322-BromoacetamideHCID 81531DiisopropylethylamineHCID 178427410HCID 178427410, compound

Product 1

HCID 595195112-[(2Z)-5-Bromo-2-[(4-methylbenzene-1-sulfonyl)imino]pyridin-1(2H)-yl]acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-[5-Bromo-1H-pyridin-(2Z)-ylidene]-4-methyl-benzenesulfonamide (80 g, 244.5 mmol) is suspended in anhydrous DMF (350 ml). Hunigs base (46.8 ml, 268.9 mmol) is added followed by 2-bromoacetamide (37.12 g, 268.9 mmol) and the mixture is stirred at room temperature for 72 hours. The reaction is poured into water (1000 ml) and the mixture is stirred for 1 hour. The product is collected by filtration, washed with more water (300 ml) and dried in a vacuum oven at 50° C. to give the title compound.

Workup

  1. stirringthe mixture is stirred for 1 hour
  2. filtrationThe product is collected by filtration
  3. washwashed with more water (300 ml)
  4. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-a2172fac4d184329a7a396fff69d131d
Source dataset
uspto-grants-2011_11
Patent number
US08053574B2

Reaction notes

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