Water → HCID 54193382, compound

HRID 2082386Notes

Reaction equation

HRID 2082386 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]([CH:18]=[N:19][C:20]([C:25]#[N:26])=[C:21]([NH2:24])[C:22]#[N:23])[CH:15]=[N:14]1.O1CCCC1.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:9])[F:10])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[N:17]=[C:16]([CH2:18][NH:19][C:20]([C:25]#[N:26])=[C:21]([NH2:24])[C:22]#[N:23])[CH:15]=[N:14]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 54054498HCID 54054498, compound

Product 1

HCID 54193382HCID 54193382, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(2-amino-1,2-dicyanoethenylimino)methyl]-2H-1,2,3-triazole (8 g) (prepared as in Example 1) was dissolved in methanol (50 ml) and tetrahydrofuran (75 ml) and then sodium borohydride (0.76 g) was added portionwise. This mixture was stirred for 20 minutes at room temperature and then poured into water to give a brown solid. This was purified by flash column chromatography to give 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-[(2-amino-1,2-dicyanoethenylamino)methyl]-2H-1,2,3-triazole, m.p. 191°-192°. A mixture of this compound (1.8 g), nicotinamide (0.6 g), N-chlorosuccinimide (0.6 g) and dimethylformamide was heated at 65°-70° for 10 minutes. The mixture was poured into water and extracted with diethyl ether. Conventional work-up and purification by flash column chromatography gave 2-(2,6-dichloro-4-trifluoromethylphenyl)-4-(4,5-dicyano-4-imidazolin-2-yl)-2H-1,2,3-triazole, m.p. 219°-220° (dec). (Compound 10).

Workup

  1. customto give a brown solid
  2. customThis was purified by flash column chromatography

Sources & evidence

ORD record
ord-85646ee9dd084cd9afdb9eec160ab5b8
Source dataset
uspto-grants-1993_02
Patent number
US05189053

Reaction notes

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