Tert-Butylamine → HCID 10832640, compound

HRID 1956711Notes

Reaction equation

HRID 1956711 reaction equation
[Br:1][C:2]1[CH:18]=[C:17]([CH3:19])[C:5]([CH2:6][NH:7][C:8]2[C:9](=O)[C:10](=[O:15])[C:11]=2[O:12]CC)=[C:4]([CH3:20])[CH:3]=1.[C:21]([NH2:25])([CH3:24])([CH3:23])[CH3:22]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:20])[C:5]([CH2:6][NH:7][C:8]2[C:11](=[O:12])[C:10](=[O:15])[C:9]=2[NH:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[C:17]([CH3:19])[CH:18]=1

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 17819425HCID 17819425, compound

Product 1

HCID 10832640HCID 10832640, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-bromo-2,6-dimethyl-benzylamino)-4-ethoxy-cyclobut-3-ene-1,2-dione (0.49 g, 1.45 mmol), t-butylamine (26 mL) and dichloromethane (8 mL) was allowed to stand at room temperature for 18 hours, then refluxed for 8 hours. The resulting solid was filtered, rinsed with acetonitrile, and dried (0.4 mm, 40° C.). This gave 0.33 g (62%) of the title compound as an off-white solid: mp 267°-271° C. (dec); 1H NMR (DMSO-d6) δ7.40 (br s, 1H), 7.32 (s, 2H), 7.30 (br t, 1H), 4.76 (d, 2H), 2.34 (s, 6H), 1.34 (s, 9H) ppm. IR (KBr): 3200, 2980, 1790, 1650 cm-1 ; MS (m/z) 364/366 (M+).

Workup

  1. temperaturerefluxed for 8 hours
  2. filtrationThe resulting solid was filtered
  3. washrinsed with acetonitrile
  4. customdried (0.4 mm, 40° C.)

Sources & evidence

ORD record
ord-d2703e3203334705b9f34def7af6fda7
Source dataset
uspto-grants-1998_07
Patent number
US05780505

Reaction notes

Loading…