Imidazole → HCID 10049710, compound

HRID 1609720Notes

Reaction equation

HRID 1609720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:20]([O-:22])=[O:21])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].N1C=CN=C1.CCOCC>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:20]([O-:22])=[O:21])[CH:5]=[C:6]([Cl:19])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[C:11]([CH:16]([CH3:18])[CH3:17])[CH:10]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 10450022HCID 10450022, compound

Product 1

HCID 10049710HCID 10049710, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,5-Dichloro-4-(3'-isopropyl-4'-hydroxyphenoxy)-nitrobenzene (10.2 g), 6.75 g. of t-butyldimethylsilyl chloride, 4.06 g of imidazole, and 2 mg of N ,N-dimethylaminopyridine in 10 ml dimethylformamide are stirred 18 hours at room temperature. The solution is poured into ether and extracted six times with water. The ether is dried, filtered and stripped to afford 3,5-dichloro-4-(3'-isopropyl-4'-t-butyldimethylsiloxyphenoxy)-nitrobenzene. NMR (CDCl3): δ0.2 (6H, s), 1.1 (9H,s), 1.2 (6H,d), 3.3 (1H,m), 6.5 (1H,d of d), 6.7 (1H,d), 8.3 (2H,s).

Workup

  1. extractionextracted six times with water
  2. dry with materialThe ether is dried
  3. filtrationfiltered

Sources & evidence

ORD record
ord-05df96569a0d4dc7b130251860c3ad26
Source dataset
uspto-grants-1995_03
Patent number
US05401772

Reaction notes

Loading…