2-Butanamine, 3,3-dimethyl- → HCID 12051670, compound

HRID 843044Notes

Reaction equation

HRID 843044 reaction equation
C(O[C:5]1[C:6](=[O:18])[C:7](=[O:17])[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)(C)C.[NH2:19][CH:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:21]>C(#N)C>[O:18]=[C:6]1[C:7](=[O:17])[C:8]([C:9]2[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[CH:13][CH:14]=2)=[C:5]1[NH:19][CH:20]([CH3:21])[C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 12051669HCID 12051669, compound

Product 1

HCID 12051670HCID 12051670, compoundYield 50.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-isopropoxy-4-(4-cyano-phenyl)-cyclobut-3-ene-1,2-dione (0.27 g, 1.12 mmol) in acetonitrile (6 mL) was added 2-amino-3,3-dimethylbutane (0.23 mL, 1.68 mmol). The mixture was stirred at room temperature overnight then filtered. The solid was recrystallized from ethyl acetate/hexanes to give 0.160 g (50%) of the title product as a white solid: m.p. 192-194° C.; 1H NMR (DMSO-d6) δ 9.01(br d,1H), 8.19(ABq,2H), 8.01(ABq,2H), 4.29(m,1H), 1.25(d,3H), 0.92(s,9H); IR (KBr) 3160, 2950, 2220, 1760, 1600, 1440, 1160, 1100, 850 cm−1; MS (m/z) 282 [M+].

Workup

  1. filtrationthen filtered
  2. customThe solid was recrystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0264d5291a6e440a9e055739e4de3225
Source dataset
uspto-grants-2002_04
Patent number
US06376555B1

Reaction notes

Loading…