Water → HCID 21914908, compound

HRID 1246513Notes

Reaction equation

HRID 1246513 reaction equation
[C-:1]#[N:2].[Na+].O.Cl[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[N:16]=[C:17]([NH:20][C:21](=[O:23])[CH3:22])[S:18][CH:19]=2)=[CH:9][CH:8]=1>CN(C=O)C>[C:1]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[N:16]=[C:17]([NH:20][C:21](=[O:23])[CH3:22])[S:18][CH:19]=2)=[CH:9][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 8929Sodium CyanideHCID 21914927N-(4-{2-[4-(chloromethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

Product 1

HCID 21914908HCID 21914908, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaCN (115 mg), KI (130 mg) and water (1.8 ml) were combined, and then a solution of N-(4-{2-[4-(chloromethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (230 mg) in DMF (7 ml) was added dropwise to the mixture at 0° C. The reaction mixture was stirred at r.t. for 19 hours, poured into water, and extracted with CHCl3. The organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residual solid was washed with ethyl ether to give N-(4-{2-[4-(cyanomethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (149.1-mg) as a colorless solid.

Workup

  1. extractionextracted with CHCl3
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. washThe residual solid was washed with ethyl ether

Sources & evidence

ORD record
ord-b26a0bfbd6d14ee3b7d51a79c81dc014
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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