HCID 60001261, compound → HCID 57493196, compound

HRID 1803833Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[NH:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[N:12]=1>C1(C)C=CC=CC=1.C(O)(=O)C.[Fe]>[NH:12]1[C:13]2[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=2[N:15]=[C:11]1[C:3]1[CH:4]=[C:5]([NH2:8])[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

Conditions

Temperature: 125 °C

Procedure

Iron powder (3.0 g, 50.9 mmol) was added to a solution of nitrobenzimidazole 7 (4.30 g, 16.9 mmol) in toluene (30 ml) and acetic acid (30 ml), and the reaction mixture was heated at 125° C. for about 1 h (completion of the reaction was monitored by TLC). The resulting crude mixture was filtered through a cotton wool plug (to remove iron particles). The crude solution was evaporated to dryness, diluted with EtOAc, washed with saturated NaHCO3 (until the pH=7), and the aqueous phase was back-extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated at reduced pressure to give 8 (2.70 g, 73%) a brown solid: 1H NMR (C2D6SO) δ 12.55 (s, 1H), 7.73(d, 1H), 7.57 (d, 1H), 7.16 (broad m, 2H), 7.09 (d, 1H), 7.01 (app d, 1H), 6.70 (dd, 1H) 5.15 (broad s, 2H), 2.39 (s, 3H); MS (ES, positive mode): 224 [M++1].

Workup

filtrationThe resulting crude mixture was filtered through a cotton wool plug (to remove iron particles)
customThe crude solution was evaporated to dryness
additiondiluted with EtOAc
washwashed with saturated NaHCO3 (until the pH=7), and the aqueous phase
extractionwas back-extracted with EtOAc
washThe combined organics were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated at reduced pressure

Sources & evidence

ORD record: ord-7bac40a3eb1b4a37906b291f20c32e2f
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354397B2

Reaction notes

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