1-(Azidomethyl)-4-methoxybenzene → Ethyl 4-(3,4-dimethoxybenzoyl)-1H-1,2,3-triazole-5-carboxylate

HRID 841963Notes

Reaction equation

COC1C=CC(CN=[N+]=[N-])=CC=1.COC1C=C(C(=O)C#CC(OCC)=O)C=CC=1OC.[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:58]=[CH:59][C:60]=1[O:61][CH3:62])[C:37]([C:39]1[N:43](CC2C=CC(OC)=CC=2)[N:42]=[N:41][C:40]=1[C:53]([O:55][CH2:56][CH3:57])=[O:54])=[O:38].COC1C=C(C=CC=1OC)C(C1N(CC2C=CC(OC)=CC=2)NNC=1C(OCC)=O)=O>C1(C)C=CC=CC=1>[CH3:32][O:33][C:34]1[CH:35]=[C:36]([CH:58]=[CH:59][C:60]=1[O:61][CH3:62])[C:37]([C:39]1[NH:43][N:42]=[N:41][C:40]=1[C:53]([O:55][CH2:56][CH3:57])=[O:54])=[O:38]

Participants

Conditions

Temperature: 100 °C

Procedure

In the same manner as in Intermediate 4, a solution of 4-methoxybenzyl azide (1.8 g) in toluene (10 ml) was added to a solution of ethyl 4-(3,4-dimethoxyphenyl)-4-oxo-2-butynoate (intermediate 2) (2.4 g, 9.2 mmol) in toluene (80 ml). The mixture was stirred at 100° C. for 18 hr. The reaction solution was concentrated under reduced pressure to give a mixture of ethyl 5-(3,4-dimethoxybenzoyl)-1-(4-methoxybenzyl)-1H-1,2,3-triazole-4-carboxylate and ethyl 4-(3,4-dimethoxybenzoyl)-3-(4-methoxybenzyl)-1H-1,2,3-triazole-5-carboxylate as an oil. The oil was used in the next reaction without purification.

Workup

concentrationThe reaction solution was concentrated under reduced pressure
customto give
customThe oil was used in the next reaction without purification

Sources & evidence

ORD record: ord-5290e9216d9249278e644035f79eca4c
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06372735B1

Reaction notes

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