2-Butanamine, 3,3-dimethyl- → 3-(4-Trifluoromethyl-phenyl)-4-(1,2,2-trimethylpropylamino)-cyclobut-3-ene-1,2-dione

HRID 991781Notes

Reaction equation

HRID 991781 reaction equation
C(O[C:5]1[C:6](=[O:20])[C:7](=[O:19])[C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)(C)C.[NH2:21][CH:22]([C:24]([CH3:27])([CH3:26])[CH3:25])[CH3:23]>>[F:18][C:15]([F:16])([F:17])[C:12]1[CH:11]=[CH:10][C:9]([C:8]2[C:7](=[O:19])[C:6](=[O:20])[C:5]=2[NH:21][CH:22]([CH3:23])[C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 5209072-Butanamine, 3,3-dimethyl-HCID 120516713-Isopropoxy-4-(4-trifluoromethyl-phenyl)-cyclobut-3-ene-1,2-dione

Product 1

HCID 99491973-(4-Trifluoromethyl-phenyl)-4-(1,2,2-trimethylpropylamino)-cyclobut-3-ene-1,2-dione

Procedure

In a manner similar to Example 9, Step 2, 3-isopropoxy-4-(4-trifluoromethyl-phenyl)-cyclobut-3-ene-1,2-dione (0.40 g, 1.408 mmol) and 2-amino-3,3-dimethylbutane (0.28 mL, 2.11 mmol) were converted to the title compound. Recrystallization from hot ethyl acetate afforded 0.18 g (39%) of compound as a white solid: m.p. 191-193° C.; 1H NMR (DMSO-d6) δ8.97(br d,1H), 8.22(ABq,2H), 7.88(ABq,2H), 4.30(m,1H), 1.26(d,3H), 0.92(s,9H); IR (KBr) 3450, 3180, 2970, 1775, 1740, 1600, 1420, 1370, 1170, 1110, 1060, 850 cm−1; MS (m/z) 325 [M+].

Sources & evidence

ORD record
ord-4dcf6f8236404b4f80b07fd0aa1b8e50
Source dataset
uspto-grants-2002_10
Patent number
US06465523B1

Reaction notes

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