Water → HCID 54182175, compound

HRID 2082393Notes

Reaction equation

HRID 2082393 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[N:17]=[C:16]([CH2:18][CH:19](SC)SC)[CH:15]=[N:14]1.BrN1C(=O)CCC1=O.O.[NH2:33]/[C:34](/[C:39]#[N:40])=[C:35](\[NH2:38])/[C:36]#[N:37]>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[N:17]=[C:16]([CH2:18][CH:19]=[N:33][C:34]([C:39]#[N:40])=[C:35]([NH2:38])[C:36]#[N:37])[CH:15]=[N:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 2723951DiaminomaleonitrileHCID 19778305HCID 19778305, compound

Product 1

HCID 54182175HCID 54182175, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(2,6-Dichloro-4-trifluoromethylphenyl)-4-[2,2-di(methylthio)ethyl]-2H-1,2,3-triazole was treated with N-bromosuccinimide in aqueous acetonitrile., After 10 minutes the mixture was added to water and extracted with diethyl ether. The extract was worked up to give crude 2-(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole-4-acetaldehyde. This was then treated with diaminomaleonitrile in a similar manner to Example 1, to give 2-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-[2-(2-amino-1,2-dicyanoethenylimino)ethyl]-2H-1,2,3-triazole, which was cyclised in a similar manner to Example 1a, to give 2-(2,6-dichloro-4-trifluoromethyl-phenyl)-4-[(4,5-dicyano-1H-imidazol-2-yl)methyl]-2H-1,2,3-triazole (Compound 30).

Workup

  1. extractionextracted with diethyl ether
  2. customto give crude 2-(2,6-dichloro-4-trifluoromethylphenyl)-2H-1,2,3-triazole-4-acetaldehyde

Sources & evidence

ORD record
ord-43eead2ca8b542218e14e0046574830f
Source dataset
uspto-grants-1993_02
Patent number
US05189053

Reaction notes

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