Aldoxime → HCID 178466047, compound

HRID 17781

Reaction equation

HRID 17781 reaction equation
N1C2C=CC=[C:9]([CH:10]=[O:11])C=2N=N1.N[C:13]1[CH:21]=[CH:20][C:16]2[NH:17][N:18]=[N:19][C:15]=2[CH:14]=1.C(=NO)C>C(Cl)Cl>[C:10]([C:13]1[CH:21]=[CH:20][C:16]2[NH:17][N:18]=[N:19][C:15]=2[CH:14]=1)(=[O:11])[CH3:9]

Participants

5

Reactant 3

HCID 7863AldoximeHCID 178507366HCID 178507366, compoundHCID 1785194492H-Benzotriazole-4-carbaldehyde

Product 1

HCID 178466047HCID 178466047, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The ketone was prepared in the same manner as the benzotriazole aldehyde from 5-aminobenzotriazole and acetaldoxime. Column chromatography of the crude ketone using DCM and eluting with MeOH (0-10%) afforded the ketone in 11% yield. Rf [A] 0.3; δH(400 MHz; Acetone-d6) 2.68 (3H, s, CH3), 7.92 (1H, d, J 8.7, Ar—H), 8.07 (1H, d, 3 8.7 Ar—H), 8.62 (1H, s, Ar—H); m/z (FAB−HR) 162.06674 [(M+H)+ calc. for C8H8N3O 162.06682]. The hydrazone of the ketone was prepared from 2,4DNPH to afford an orange solid. 4,6-Dinitro-7-1H-benzotriazole [26]

Workup

  1. washeluting with MeOH (0-10%)

Sources & evidence

ORD record
ord-b0801a99f04f4e83a219a0e7897fc984
Source dataset
uspto-grants-2010_06
Patent number
US07741102B2

Linked notes

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