Ammonium Hydroxide → HCID 21069730, compound

HRID 915874Notes

Reaction equation

HRID 915874 reaction equation
Cl[C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C@@H:12]3[O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])[C@@H:15]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[C@@:13]3([CH3:39])[OH:14])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH4+:40].[OH-]>O1CCOCC1>[NH2:40][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([C@@H:12]3[O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=4[Cl:38])[C@@H:15]([O:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=4[Cl:25])[C@@:13]3([CH3:39])[OH:14])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 21069731HCID 21069731, compound

Product 1

HCID 21069730HCID 21069730, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a compound 6.2 (5 g, 6.7 mmol) in dioxane (100 mL) was added conc. NH4OH (100 mL). The mixture was heated in a stainless steel autoclave at 100° C. for 3 h, then cooled and evaporated in vacuo. The crude mixture was dissolved in 100 mL of CH2Cl2 and washed with water and brine, dried over MgSO4, filtered and concentrated to provide crude product. The crude product was then purified on a silica gel column with 5% MeOH in CH2Cl2 as eluent to give 4.32 g of 6.3 as white foam (yield 88%).

Workup

  1. temperaturecooled
  2. customevaporated in vacuo
  3. dissolutionThe crude mixture was dissolved in 100 mL of CH2Cl2
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto provide crude product
  9. customThe crude product was then purified on a silica gel column with 5% MeOH in CH2Cl2 as eluent

Sources & evidence

ORD record
ord-2a3dc2e327704efcbb6c1e59df05ebda
Source dataset
uspto-grants-2007_09
Patent number
US07268119B2

Reaction notes

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