2-Fluoro-1H-benzimidazole → HCID 86739840, compound
Reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[NH2:12][CH:13]1[C:24](=[O:25])[N:15]2[CH:16]([C:21]([OH:23])=[O:22])[C:17]([CH3:20])([CH3:19])[S:18][C@H:14]12.F[C:27]1[NH:28][C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[N:31]=1>CN(C=O)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[N:28]1[C:29]2[CH:35]=[CH:34][CH:33]=[CH:32][C:30]=2[NH:31][C:27]=1[NH:12][CH:13]1[C:24](=[O:25])[N:15]2[CH:16]([C:21]([OH:23])=[O:22])[C:17]([CH3:20])([CH3:19])[S:18][C@H:14]12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of anhydrous 6-amino-2,2-dimethylpenam-3-carboxylic acid toluene-p-sulphonate (171 mg.) in dry DMF was added 2-fluorobenzimidazole (150 mg.) in one portion and the mixture stirred at ambient temperature for 1.5 hours. The mixture was evaporated to dryness under reduced pressure at room temperature and the resulting residue, a mobile oil, was triturated with EtOAc (2×10 ml.) and then dry acetonitrile (2 ml.) whereupon the product crystallised. The solid was filtered and washed with acetonitrile and ether to give 6-(benzimidazol-2-yl)amino-2,2-dimethylpenam-3-carboxylic acid toluene-p-sulphonate (185 mg.), m.p. 181°-183°, having the following n.m.r. spectrum in d6DMSO: 1.49 (s, 3H); 1.62 (s, 3H); 2.29 (s, 3H); 4.39 (s, 1H); 5.54 (br, 1H); 5.68 (d, 1H); 7.0-7.56 (m, 8H); 9.93 (br, 1H).