4-Methylmorpholine → 59177-46-7

To a stirred solution of 4-mercaptobenzoic acid (1.00 g, 6.49 mmol) and N-methylmorpholine (0.78 ml, 7.14 mmol) in ethyleneglycol dimethylether (20 ml) was added iso-butylchloroformate (0.92 ml, 7.14 mmol). The reaction was stirred at ambient temperature overnight and filtered to a clear pale yellow solution which was treated with excess ammonia as a solution in dioxane (0.5M, ˜15 ml). This solution was stirred for two hours at room temperature, and concentrated in vacuo to a white solid. The solid was dissolved in a mixture of H2O (10 ml) and CHCl3 (30 ml), the aqueous was basified using 2N NaOH(aq) and the organic layer separated and dried (MgSO4) before being concentrated in vacuo to a white solid (679 mg). The solid was treated with a solution of sodium methoxide in methanol (10 ml) and when TLC showed no more starting material, the reaction was acidified using 2N HCl(aq) to pH=4, then concentrated in vacuo. The residue was treated with water and extracted with CHCl3, then concentrated in vacuo to give the title compound as an off white solid (376 mg).

1. filtrationfiltered to a clear pale yellow solution which
2. additionwas treated with excess ammonia as a solution in dioxane (0.5M, ˜15 ml)
3. stirringThis solution was stirred for two hours at room temperature
4. concentrationconcentrated in vacuo to a white solid
5. dissolutionThe solid was dissolved in a mixture of H2O (10 ml) and CHCl3 (30 ml)
6. customthe organic layer separated
7. dry with materialdried (MgSO4)
8. concentrationbefore being concentrated in vacuo to a white solid (679 mg)
9. additionThe solid was treated with a solution of sodium methoxide in methanol (10 ml) and when TLC
10. concentrationconcentrated in vacuo
11. additionThe residue was treated with water
12. extractionextracted with CHCl3
13. concentrationconcentrated in vacuo

ORD record

ord-32affd0621674d65849e4f077fe80e33

Source dataset

uspto-grants-2006_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07148236B2