Methyl chloroacetate → methyl 2-(5-amino-2H-1,2,3,4-tetrazol-2-yl)acetate

63.1 A solution of 8.5 g 5-amino-1H-tetrazole, 8.8 ml methyl chloroacetate and 5.8 g potassium hydroxide in 100 ml methanol was heated to reflux under an argon atmosphere and stirred for 18 h. A white solid slowly precipitated. The suspension was cooled to r.t. The white solid was filtered off and washed with methanol. The filtrate was concentrated. The residue was suspended in 100 ml EtOH and heated to reflux. After 1 h stirring at reflux, the mixture was filtered while hot. The filtrate was concentrated. The residue was recrystallized in 100 ml EtOH to give 1.8 g of (5-amino-tetrazol-2-yl)-acetic acid methyl ester as colorless crystalline solid.

1. temperatureto reflux under an argon atmosphere
2. customA white solid slowly precipitated
3. filtrationThe white solid was filtered off
4. washwashed with methanol
5. concentrationThe filtrate was concentrated
6. temperatureheated to reflux
7. stirringAfter 1 h stirring
8. temperatureat reflux
9. filtrationthe mixture was filtered while hot
10. concentrationThe filtrate was concentrated
11. customThe residue was recrystallized in 100 ml EtOH

ORD record

ord-cf0a1d2e1922465885dc3af24dd031b0

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361672B2