Triethylamine → N-(1-Hydroxy-2-methylpropan-2-yl)-2-methoxybenzamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.N1C=CN=N1.OC1(C=CC=CC1)C(O)=O.[OH:27][CH2:28][C:29]([NH2:32])([CH3:31])[CH3:30].C(N(CC)CC)C>C(Cl)Cl.O>[OH:27][CH2:28][C:29]([NH:32][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[O:2][CH3:1])([CH3:31])[CH3:30]Participants
Procedure
15.2 g (100 mmol) of 2-methoxy-benzoic acid are dissolved in 300 ml of methylene chloride and the solution is stirred with 14.2 g (105 mmol) of 1-hydroxy-benzoic acid triazole×1 H2O and 21.66 g (105 mmol) of N,N-dicyclohexylcarbodiimide at 0° C. The suspension thus obtained is stirred at room temperature for 0.5 hour, cooled to 0° C. again, and a solution of 9.89 g (111 mmol) of 1-hydroxy-2-methyl-2-propylamine and 12.65 g (125 mmol) of triethylamine in 300 ml of methylene chloride is added. The reaction is complete after 1 hour. The reaction mixture is washed with 1M of hydrochloric acid and saturated sodium bicarbonate solution, dried over sodium sulphate and concentrated in vacuo. The crude product is stirred with petroleum ether, filtered off with suction, subsequently rinsed with the solvent and dried under a high vacuum.
Workup
- customThe suspension thus obtained
- temperaturecooled to 0° C. again
- waitThe reaction is complete after 1 hour
- washThe reaction mixture is washed with 1M of hydrochloric acid and saturated sodium bicarbonate solution
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
- stirringThe crude product is stirred with petroleum ether
- filtrationfiltered off with suction
- washsubsequently rinsed with the solvent
- customdried under a high vacuum
Sources & evidence
- ORD record
- ord-f2496074f91240a19a3ec732862e7cdd
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05596006
Reaction notes
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