2-Bromo-N-ethylacetamide → HCID 135828226, compound

HRID 720451Notes

Reaction equation

HRID 720451 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[C:5]([C:17]#[N:18])=[C:4]([SH:19])[N:3]=1.[CH2:20]([NH:22][C:23](=[O:26])[CH2:24]Br)[CH3:21].C([O-])(O)=O.[Na+]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[C:4]([S:19][CH2:24][C:23]([NH:22][CH2:20][CH3:21])=[O:26])[C:5]([C:17]#[N:18])=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 2207922-Bromo-N-ethylacetamideHCID 516892Sodium BicarbonateHCID 178510481HCID 178510481, compound

Product 1

HCID 135828226HCID 135828226, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At RT 0.76 g (2 mmol) of 2-amino-4-(4-hydroxyphenyl)-6-sulfanyl-3,5-pyridinedicarbonitrile and 0.5 g (3 mmol) of N-ethylbromoacetamide are stirred in 5 ml of DMF together with 0.34 g (4 mmol) of NaHCO3 for 4 hours. After dilution with water, the mixture is extracted with ethyl acetate and the ethyl acetate phase is dried with MgSO4 and concentrated under reduced pressure. The solid residue obtained after concentration is stirred with methanol. The crystals are filtered off with suction and dried under reduced pressure.

Workup

  1. extractionAfter dilution with water, the mixture is extracted with ethyl acetate
  2. dry with materialthe ethyl acetate phase is dried with MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe solid residue obtained
  5. concentrationafter concentration
  6. filtrationThe crystals are filtered off with suction
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-7ac6ea661a9442ca9e2a1260ec8ddce6
Source dataset
uspto-grants-2006_11
Patent number
US07135486B1

Reaction notes

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