2-Amino-2-methyl-1-propanol → 2-{[4-(4-Nitrophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol

HRID 1436418Notes

Reaction equation

HRID 1436418 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=2)[N:6]=1.[NH2:16][C:17]([CH3:21])([CH3:20])[CH2:18][OH:19]>>[N+:13]([C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:6]=[C:2]([NH:16][C:17]([CH3:21])([CH3:20])[CH2:18][OH:19])[S:3][CH:4]=2)=[CH:8][CH:9]=1)([O-:15])=[O:14]

Participants

3

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 68902424HCID 68902424, compound

Product 1

HCID 866186072-{[4-(4-Nitrophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-olYield 69%

Conditions

Temperature
175 °C

Procedure

2-Bromo-4-(4-nitrophenyl)-1,3-thiazole (1.0 g, 3.5 mmol), prepared in the previous step, and 2-amino-2-methyl-propan-1-ol (2.0 mL, 21.0 mmol) were placed in a sealed tube and heated to 175° C. for 18 h. The crude product was pre-adsorbed onto silica gel and purified using a stepwise gradient of 1-5% methanol:methylene chloride to give 2-{[4-(4-nitrophenyl)-1,3-thiazol-2-yl]amino}-2-methylpropan-1-ol (700 mg, 69%), MS (ES) m/z 294[M+H]+.

Workup

  1. customwere placed in a sealed tube
  2. custompurified

Sources & evidence

ORD record
ord-4cb6ec4c33fe481198c4edb6d896d94d
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

Loading…