Ammonia → HCID 22491695, compound

HRID 2180222Notes

Reaction equation

HRID 2180222 reaction equation
[CH:1]1[N:5]([CH2:6][O:7][CH2:8][CH2:9][OH:10])[C:4]2[N:11]=[C:12]([NH2:16])[N:13]=[C:14]([OH:15])[C:3]=2[N:2]=1.[H-].[Na+].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)=O.N>CN(C=O)C>[OH:10][CH2:9][CH2:8][O:7][CH2:6][N:5]1[C:4]2[N:11]=[C:12]3[N:13]([CH:20]=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)[NH:16]3)[C:14](=[O:15])[C:3]=2[N:2]=[CH:1]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24758Sodium hydrideHCID 68303p-Chlorophenacyl bromideHCID 178508933HCID 178508933, compound

Product 1

HCID 22491695HCID 22491695, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.4 g (6.22 mmol) acyclovir, 30 mL DMF, and 400 mg sodium hydride (80%) was stirred at room temperature for 30 min, then 0.7 mL 2-bromo-4′-chloroacetophenone was added dropwise into the solution. Changing to orange color, the solution was added 17 mL ammonia, and continuously stirred for 5 hr. The solvent was removed to obtain a residue, which was washed with water. The product, 3-(2-hydroxy-ethoxymethyl)-6-(4-chlorophenyl)-3,5-dihydro-1,3,4,5,7a-pentaaza-s-indacen-8-one, was produced and weighted 1.62 g (white solid, yield 72%).

Workup

  1. customThe solvent was removed
  2. customto obtain a residue, which
  3. washwas washed with water

Sources & evidence

ORD record
ord-363283d716334c30af74de79a9d9ffa7
Source dataset
uspto-grants-2005_05
Patent number
US06887997B2

Reaction notes

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