Hydrochloric Acid → HCID 53702257, compound

HRID 1681848Notes

Reaction equation

HRID 1681848 reaction equation
[ClH:1].[CH3:2][C:3]([CH3:15])([CH3:14])[C:4](O)([CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1)[C:5]#[CH:6].[Br:16]N1C(=O)CCC1=O.[OH-:24].[Na+]>C(Cl)Cl>[Br:16][CH:6]=[C:5]([Cl:1])[C:4]([OH:24])([CH2:7][N:8]1[CH:12]=[N:11][CH:10]=[N:9]1)[C:3]([CH3:15])([CH3:14])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 14328501HCID 14328501, compound

Product 1

HCID 53702257HCID 53702257, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Hydrogen chloride gas is passed into a solution of 1.93 g (10 mmol) of 4,4-dimethyl-3-hydroxy-3-[(1,2,4-triazol-1-yl)-methyl]-1-pentine in 30 ml of methylene chloride at -20° C. until saturation is reached. 1.8 g (20 mmol) of N-bromosuccinimide are then added in portions and the mixture is subsequently stirred at 0° C. for 1 hour and at room temperature for 12 hours. HCl and solvent are stripped off in vacuo and the residue is worked up with methylene chloride and dilute sodium hydroxide solution. 2.1 g (68% of theory) of 1-bromo-2-chloro-4,4-dimethyl-3-hydroxy-3-((1,2,4-triazol-1-yl)-methyl]-1-pentene are thus obtained as a mixture of isomers of melting point 45°-48° C.

Sources & evidence

ORD record
ord-1d0c91f7e5d8478bb5b82e1c2761d617
Source dataset
uspto-grants-1992_12
Patent number
US05175169

Reaction notes

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