Ammonia → HCID 511650, compound

HRID 2180223Notes

Reaction equation

HRID 2180223 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]([Br: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]([Br: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 74544-Bromophenacyl bromideHCID 24758Sodium hydrideHCID 178508933HCID 178508933, compound

Product 1

HCID 511650HCID 511650, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.7 g acyclovir, 70 mL DMF, and 800 mg sodium hydride (80%) was stirred at room temperature for 15 min, then 4 g 2,4′-dibromo-acetophenone was added into the solution. The solution was stirred at room temperature for 3 hr, added 15 mL ammonia, and was continuously stirred overnight. The solvent was removed to obtain a residue, which was washed with 50 mL of water and acetone to produce a product, 3-(2-hydroxy-ethoxymethyl)-6-(4-bromophenyl)-3,5-dihydro-1,3,4,5,7a-pentaaza-s-indacen-8-one, 2.55 g (yellow, yield 53%).

Workup

  1. waitwas continuously stirred overnight
  2. customThe solvent was removed
  3. customto obtain a residue, which
  4. washwas washed with 50 mL of water and acetone

Sources & evidence

ORD record
ord-86aec6e1f923410782bf63a9e7385cd8
Source dataset
uspto-grants-2005_05
Patent number
US06887997B2

Reaction notes

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