Carbon Tetrachloride → 113274-30-9

A solution of triphenylphosphine (5.89 g, 2.25×10-2 mol) and 3-carboethoxy-1-(2 hydroxyethyl)-3-methyltriazene, 5b, (2.9 g, 2.0×10 -2 mol) in 50 mL of carbon tetrachloride (dried over 3A molecular sieves) was refluxed overnight under nitrogen. The reaction mixture was cooled to room temperature and diluted with pentane (250 mL). After standing at 10° C. overnight, the reaction mixture was filtered through a pad of Celite to remove precipitated triphenylphosphine oxide. The filtrate was concentrated on a rotary evaporator at 220° C., the residue (4.2 g) was dissolved in a minimum amount of ether and chromatographed on a column of 35 g of Silica Gel 60 packed in 10% ether in pentane and eluted with 600 mL of this same solvent mixture. Evaporation of the eluent on a rotary evaporator and vacuum transfer (40° C./0.005 mm) of the residue gave 1.94 g 0.0119 mol, 59.6%) of 3-acetyl-1-(2-chloroethyl)-3-methyltriazene, 6b; IR (CCl4) 2970, 1710, 1515, 1145, 990 cm10-1 ; UV (CH3CN) λmax 238 (log ε 4.23); 1H NMR (CDCl3, Me4Si) δ 3.45 (CH3,s), 3.23 (N--CH3, s), 3.90 (Cl--CH2,t,J=5.5 Hz), 4.12 (CH2 -N,t,J=5.5 Hz); proton decoupled 13C NMR (CDCl3, Me4Si) δ 21.85 (CH3 (, 26.92 (N--C H3), 41.78 Cl--CH2), 62.68 (CH2 --N), 63.17 (0--CH2CH3), 173.0 (C=0); exact mass calcd. m/z for C5H10N3OC1 163.0512, found 163.0506 (by EI).

1. filtrationthe reaction mixture was filtered through a pad of Celite
2. customto remove
3. customprecipitated triphenylphosphine oxide
4. concentrationThe filtrate was concentrated on a rotary evaporator at 220° C.
5. dissolutionthe residue (4.2 g) was dissolved in a minimum amount of ether
6. customchromatographed on a column of 35 g of Silica Gel 60
7. washeluted with 600 mL of this same solvent mixture
8. customEvaporation of the eluent
9. customon a rotary evaporator and vacuum transfer (40° C./0.005 mm) of the residue

ORD record

ord-223dc6a6746d418d8962783befe80148

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04923970