Sodium Hydroxide → HCID 178441999, compound

HRID 1357241Notes

Reaction equation

HRID 1357241 reaction equation
[C:1]([CH2:3][O:4][C:5]1[C:6]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)=[C:7]2[C:12](=[CH:13][CH:14]=1)[CH:11]=[C:10]([CH2:15][NH:16][C:17]([C:19]1[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[O:21][C:20]=1[CH2:28][CH2:29][CH2:30][CH3:31])=[O:18])[CH:9]=[CH:8]2)#[N:2].[N-:39]=[N+:40]=[N-:41].[Na+].[Cl-].[NH4+].[OH-].[Na+]>CN(C=O)C.O>[NH:39]1[C:1]([CH2:3][O:4][C:5]2[C:6]([C:32]3[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=3)=[C:7]3[C:12](=[CH:13][CH:14]=2)[CH:11]=[C:10]([CH2:15][NH:16][C:17]([C:19]2[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[O:21][C:20]=2[CH2:28][CH2:29][CH2:30][CH3:31])=[O:18])[CH:9]=[CH:8]3)=[N:2][N:41]=[N:40]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 12083563HCID 12083563, compound

Product 1

HCID 178441999HCID 178441999, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid (6-cyanomethoxy-5-p-tolyl-naphthalen-2-ylmethyl)-amide (182 mg, 0.36 mmol), prepared in the previous step, sodium azide (77.6 mg, 1.19 mmol) and ammonium chloride (102 mg, 1.90 mmol) in 10 mL of DMF was stirred under nitrogen at 100° C. for 21 h (overnight). If starting material remains additional sodium azide and ammonium chloride are added and the stirring continued at 100° C. until the reaction is complete. The reaction was diluted with water, made basic by the addition of 1 N NaOH and extracted multiple times with ethyl acetate. The ethyl acetate extracts were combined, acidified with 1 N HCl and then concentrated under reduced pressure. The solid present was collected by filtration and dried under reduced pressure to give the title compound (130 mg, 66%) as a white solid, mp 162-166° C.

Workup

  1. additionare added
  2. customcontinued at 100° C. until the reaction
  3. extractionextracted multiple times with ethyl acetate
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe solid present was collected by filtration
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-a22a0493935240c381f780bbd80c1172
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

Loading…