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

HRID 1784904Notes

Reaction equation

HRID 1784904 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-78fedb32620646d5b1f94b66e481d520
Source dataset
uspto-grants-2009_03
Patent number
US07504421B2

Reaction notes

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