Anisole → HCID 178470514, compound

HRID 1794683Notes

Reaction equation

C1(OC)C=CC=CC=1.COC1C=CC(C[N:16]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([C:26](=[O:40])[C:27]3[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[CH:29][C:28]=3[N+:37]([O-:39])=[O:38])[N:18]=[N:17]2)=CC=1.COC1C=CC(CN2C(C(=O)C3C=C(OC)C(OC)=CC=3[N+]([O-])=O)=C(C(OCC)=O)N=N2)=CC=1>FC(F)(F)C(O)=O>[CH3:36][O:35][C:30]1[C:31]([O:33][CH3:34])=[CH:32][C:27]([C:26]([C:19]2[NH:18][N:17]=[N:16][C:20]=2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:40])=[C:28]([N+:37]([O-:39])=[O:38])[CH:29]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Anisole (1 ml) was added to a solution of an about 1:1 mixture (4.4 g) of ethyl 1-(4-methoxybenzyl)-4-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-5-carboxylate (Synthesis Example 1, b-1) and ethyl 1-(4-methoxybenzyl)-5-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate(Synthesis Example 1, b-2) in trifluoroacetic acid (10 ml), and the mixture was stirred at 60° C. for 10 hr. After the mixture was allowed to stand for cooling, the solvent was evaporated under reduced pressure, followed by azeotropic evaporation using toluene. The resultant crystal was collected by filtration, washed with diethyl ether, and then dried to give ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (3.12 g, 95%).

Workup

temperaturefor cooling
customthe solvent was evaporated under reduced pressure
customfollowed by azeotropic evaporation
filtrationThe resultant crystal was collected by filtration
washwashed with diethyl ether
customdried

Sources & evidence

ORD record: ord-45f272dfcf1c4f3aaa16b9d43e8b97cc
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022860B2

Reaction notes

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