Reaktion #1771286

Reaktionsgleichung

bromoacetyl chloride

KBr

pyridine

9

3,6-Bis(methylcarbamyl)-1,4-dimethoxy-2,5-diaminobenzene

dimethyl formamide

→

2,5 -Bis(bromoacetamido)-3,6-bis(methylcarbamyl)-1,4-dimethoxybenzene

Lösungsmittel

n-butanol acetic acid water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe precipitated product was filtered off
2. 2
   Waschenrinsed with water
3. 3
   Waschenrinsed with ethanol
4. 4
   Sonstige393 mg (53%) yield

Vorschrift

To a solution of 503 mg (1.42 mmol) of 9 .2HCl in 15 mL of dry dimethyl formamide were added sequentially, 533 μL (6.59 mmol) of pyridine and 282 μL (3.42 mmol) of bromoacetyl chloride. After allowing the mixture to stir at room temperature for 6 hours, the precipitated product was filtered off and rinsed with water and then rinsed with ethanol: 393 mg (53%) yield; mp 308°-310° C.; TLC (n-butanol/acetic acid/water [5:2:3]), Rf =0.58; IR (KBr pellet) 3380, 3278, 1681, 1638, 1551, 1472, 1411, 1325, 1238, 1047 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ9.72 (2H, s, 2- and 5-acetamido N(H), 7.87 (2H, brs, 3- and 6-carbamyl proton), 4.22 (4H, s, methylenes), 3.65 (6H, s, methoxys), 2.70 (6H, d, J=4.6 Hz, 3- and 6-carbamyl methyl); mass spectrum (EI mode) m/z 522, 524 and 526 (P+ for the 79Br, 79Br; 79Br, 81Br; 81Br, 81Br combinations, respectively, at an intensity ratio of 1:2:1).

Quelle