Ammonia → Ethyl-[2-amino-3-nitro-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate

HRID 639626Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[N:5]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=[C:15](Cl)[C:14]=1[N+:24]([O-:26])=[O:25])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].[NH3:28]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:27])[N:5]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=[C:15]([NH2:28])[C:14]=1[N+:24]([O-:26])=[O:25])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl-[2-chloro-3-nitro-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate (63 gm 160 mmol) was dissolved in tetrahydrofuran (300 mL) and to this was added 0.880 ammonia solution (100 mL) to give two phases. This was transferred to a pressure vessel, sealed and heated to 80° C. with stirring for 2 hours. The tetrahydrofuran was evaporated and the residue was partitioned between saturated brine and diethyl ether. The organic extracts were dried over sodium sulphate, filtered and evaporated to give a thick yellow slurry (65 gm) of crude product.

Workup

customto give two phases
customThis was transferred to a pressure vessel
customsealed
customThe tetrahydrofuran was evaporated
customthe residue was partitioned between saturated brine and diethyl ether
dry with materialThe organic extracts were dried over sodium sulphate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-06a876a9a9284697bf2d805258fdceaf
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691877B2

Reaction notes

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