Sodium Hydroxide → HCID 178442000, compound

HRID 1357246Notes

Reaction equation

HRID 1357246 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]([O:21][CH2:22][C:23]#[N:24])=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15]([CH2:25][NH:26][C:27]([C:29]2[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[O:31][C:30]=2[CH2:38][CH2:39][CH2:40][CH3:41])=[O:28])=[CH:16]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[N-:42]=[N+:43]=[N-:44].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:20]([O:21][CH2:22][C:23]3[NH:44][N:43]=[N:42][N:24]=3)=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15]([CH2:25][NH:26][C:27]([C:29]2[C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[O:31][C:30]=2[CH2:38][CH2:39][CH2:40][CH3:41])=[O:28])=[CH:16]3)=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 86587382HCID 86587382, compound

Product 1

HCID 178442000HCID 178442000, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid [5-(4-tert-butyl-phenyl)-6-cyanomethoxy-naphthalen-2-ylmethyl]-amide (207 mg, 0.38 mmol), prepared in the previous step, sodium azide (72.9 mg, 1.12 mmol) and ammonium chloride (58,7 mg, 1.10 mmol) in 10 mL of DMF was stirred under nitrogen at 100° C. for 6 h. If starting material remains additional quantities of sodium azide and ammonium chloride are added until the reaction is complete by TLC. The reaction was diluted with water, made basic by the addition of 1 N NaOH and extracted multiple times with ethyl acetate. The combined organic extracts were acidified by the addition of 1 N HCl and then concentrated under reduced pressure. The residue was diluted with water and the solid that formed was collected by filtration and dried under reduced pressure to give the title compound (186 mg, 84%) as a white solid, mp75-78° C.

Workup

  1. additionare added until the reaction
  2. extractionextracted multiple times with ethyl acetate
  3. additionThe combined organic extracts were acidified by the addition of 1 N HCl
  4. concentrationconcentrated under reduced pressure
  5. additionThe residue was diluted with water
  6. customthe solid that formed
  7. filtrationwas collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-7db58889604244f29c888ebd87df332d
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…