تفاعل #1694

معادلة التفاعل

1,4,5,6-tetrahydropyrimidine-5-carboxylic acid hydrochloride

oxalyl chloride

2-butyn-l-ol

→

5-(2-butynyloxycarbonyl)-1,4,5,6-tetrahydropyrimidine

المردود 61.0%

المذيبات

water

benzene

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةunder reflux for 2.5 h
3. 3
   أخرىevaporated to dryness in vacuo
4. 4
   درجة الحرارةafter cooling
5. 5
   أخرىto give an orange-yellow residue
6. 6
   workup.STIRRINGwas stirred at room temperature overnight
7. 7
   workup.STIRRINGAfter stirring overnight
8. 8
   أخرىthe solvents were removed in vacuo
9. 9
   أخرىto give a brownish residue
10. 10
    workup.STIRRINGstirred at room temperature for 2 h
11. 11
    ترشيحfiltered
12. 12
    أخرىThe brown residue obtained on removal of the solvents in vacuo
13. 13
    أخرىwas recrystallized (ethanol/ether)

الإجراء التجريبي

1,4,5,6-tetrahydropyrimidine-5-carboxylic acid hydrochloride (1 g, 6 mmol) was suspended in a solution of oxalyl chloride (1.5 mL, 17 mmol) in benzene (10 mL), heated with stirring under reflux for 2.5 h, and then evaporated to dryness in vacuo after cooling, to give an orange-yellow residue. A mixture of the acid chloride (04 g) and 2-butyn-l-ol (20 mL, excess) was stirred at room temperature overnight. After stirring overnight, the solvents were removed in vacuo to give a brownish residue. The residue was taken up in water (100 mL), stirred at room temperature for 2 h and filtered. The brown residue obtained on removal of the solvents in vacuo was recrystallized (ethanol/ether) to give a brown viscous oil (0.3 g, 61%) of 5-(2-butynyloxycarbonyl)-1,4,5,6-tetrahydropyrimidine as the hydrochloride salt. 1H NMR (D2O): δ 1.5 (t, 3H, CH3), 3.1 (m, 1H), 3.5 (d, 4H), 3.9 (q, 2H, OCH2), 7.9 (s, 1H, amidine-H). Anal. (C9H13N2O2Cl) C, H, N.

المصدر