Propyl p-toluenesulfonate → p-Toluenesulfonic acid
Reaction equation
[S:1]([C:8]1[CH:14]=[CH:13][C:11]([CH3:12])=[CH:10][CH:9]=1)([O:4]CCC)(=[O:3])=[O:2]>CN(C)C=O>[CH3:12][C:11]1[CH:13]=[CH:14][C:8]([S:1]([OH:4])(=[O:3])=[O:2])=[CH:9][CH:10]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
A 12 L, three necked flask was equipped with an overhead stirrer, a temperature probe, a heating mantle, a claisen joint, a condenser, and a 500 ml addition funnel. The flask was charged with 250 grams of R(+)-2,6 diamino-4,5,6,7-tetrahydro-benzothiazole (R(+) diamine), followed by 2 L of dimethyl formamide (DMF). Under continuous stirring, the mixture was heated to a temperature of 65° C. The addition funnel was charged with a solution of 386.6 grams propyl tosylate (1.25 molar equivalents) and 322 ml diisopropylethyleamine (1.25 molar equivalents) in 500 ml DMF. This solution was added to the 12 L flask dropwise over a period of 2.0 hours. The reaction was monitored by analysis on HPLC.
Workup
- customA 12 L, three necked flask was equipped with an overhead stirrer
- additiona temperature probe, a heating mantle, a claisen joint, a condenser, and a 500 ml addition funnel
- additionThis solution was added to the 12 L flask dropwise over a period of 2.0 hours
Sources & evidence
- ORD record
- ord-a5fea26026064afdac0acd6239aa65d2
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524695B2
Reaction notes
Loading…