Imidazole → 4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloroaniline

HRID 630390Notes

Reaction equation

HRID 630390 reaction equation
NC1C=CC(CO)=CC=1Cl.Cl[Si](C(C)(C)C)(C)C.N1C=CN=C1.[Si:24]([O:31][CH2:32][C:33]1[C:39](OC)=[CH:38][C:36]([NH2:37])=[C:35]([Cl:42])[CH:34]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]>CN(C=O)C>[Si:24]([O:31][CH2:32][C:33]1[CH:39]=[CH:38][C:36]([NH2:37])=[C:35]([Cl:42])[CH:34]=1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 13843958(4-Amino-3-chlorophenyl)methanol2×HCID 671456574-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloro-5-methoxyaniline

Product 1

HCID 671452954-({[Tert-butyl(dimethyl)silyl]oxy}methyl)-2-chloroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Obtained as a light orange oil (87%) starting from (4-Amino-3-chlorophenyl)methanol (intermediate 45; 2.72 g, 0.016 mol), 4.94 g (0.033 mmol) of cloro(tertbutyl)-dimethylsilane and 3.35 g (0.049 mol) of imidazole in 68 ml DMF and following the experimental procedure as described for intermediate 39.

Sources & evidence

ORD record
ord-e5fdf61f8e9145a99cc6dba5d126698a
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

Loading…