Water → HCID 22025153, compound

HRID 1792772Notes

Reaction equation

HRID 1792772 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:19]=[CH:18][C:13]3[O:14][CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([SH:22])[N:3]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+].O>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:19]=[CH:18][C:13]3[O:14][CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 516892Sodium BicarbonateHCID 178510472HCID 178510472, compound

Product 1

HCID 22025153HCID 22025153, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.32 mol) of 2-amino-6-sulfanyl-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-3,5-pyridinedicarbonitrile [prepared analogously to Dyachenko et al., Russian Journal of Chemistry 33 (7), 1014–1017 (1997); 34 (4), 557–563 (1998)], 110 mg (0.64 mmol) of benzyl bromide and 108 mg (1.29 mmol) of sodium bicarbonate are stirred in 2 ml of DMF at room temperature for 5.5 h. Water is then added and the mixture is extracted three times with ethyl acetate. The combined organic phases are dried with magnesium sulfate and concentrated under reduced pressure. The residue is taken up in diethyl ether, giving, after reconcentration, a crystalline product.

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. dry with materialThe combined organic phases are dried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customgiving

Sources & evidence

ORD record
ord-84b5791973bb4e4b97ae5ec3d0a3b7e3
Source dataset
uspto-grants-2006_07
Patent number
US07078417B2

Reaction notes

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