Tert-Butylamine → 3-Tert-butylamino-4-[(5-nitro-benzofuran-2-ylmethyl)-amino]-cyclobut-3-ene-1,2-dione

HRID 363003Notes

Reaction equation

C(O[C:6]1[C:7](=[O:25])[C:8](=[O:24])[C:9]=1[NH:10][CH2:11][C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=2[CH:16]=1)CCC.[C:26]([NH2:30])([CH3:29])([CH3:28])[CH3:27]>C(O)C>[C:26]([NH:30][C:6]1[C:7](=[O:25])[C:8](=[O:24])[C:9]=1[NH:10][CH2:11][C:12]1[O:13][C:14]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:15]=2[CH:16]=1)([CH3:29])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: 70 °C

Procedure

To 3-butoxy-4-[(5-nitro-benzofuran-2-ylmethyl)amino]-cyclobut-3-ene-1,2-dione (0.25 g, 0.727 mmol), as prepared in Example 8, in ethanol (5 mL) was added tert-butylamine (0.51 mL, 4.85 mmol). The reaction was stirred at 70° C. for 18 hours and then at room temperature for 48 hours. Workup in a manner identical to Example 9 afforded 0.20 g (80%) of 3-tert-butylamino-4-[(5-nitro-benzofuran-2-ylmethyl)-amino]-cyclobut-3-ene-1,2-dione as an off-white solid: mp>300° C.; 1H NMR (DMSO-d6): δ 8.61 (d, 1H), 8.20 (dd, 1H), 7.91 (br t, 1H), 7.81 (d, 1H), 7.59 (br s, 1H), 7.07 (s, 1H), 4.98 (d, 2H), 1.36 (s, 9H). IR (KBr): 3220, 2930, 1800, 1675 cm-1 ; MS (m/z) 344.3 [M+H]+.

Workup

waitat room temperature for 48 hours

Sources & evidence

ORD record: ord-e7e68f9636e640c690d7b3d20770243f
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872139

Reaction notes

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