Sodium Hydroxide → HCID 178442001, compound

HRID 1357244Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-butyl-benzofuran-3-carboxylic acid [5-(4-chloro-phenyl)-6-cyanomethoxy-naphthalen-2-ylmethyl]-amide (152 mg, 0.29 mmol), prepared in the previous step, sodium azide (59 mg, 0.90 mmol) and ammonium chloride (85 mg, 1.58 mmol) in 10 mL of DMF was stirred under nitrogen at 100° C. for 24 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 50 mL of water, made basic by the addition of 1 N NaOH and extracted multiple times with ethyl acetate. The aqueous layer was acidified. The solid that formed was collected by filtration and dried under reduced pressure to give the title compound (149 mg, 91%) as a white solid, mp 208-211° C.

Workup

additionare added
customcontinued at 100° C. until the reaction
extractionextracted multiple times with ethyl acetate
customThe solid that formed
filtrationwas collected by filtration
customdried under reduced pressure

Sources & evidence

ORD record: ord-3d84d502c99545f285a8946b5af9f44a
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06589970B2

Reaction notes

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