Potassium Carbonate → N,N-Bis((5-chlorobenzo[b]thiophen-3-yl)methyl)-1H-benzo[d]imidazol-5-amine

HRID 45953Notes

Reaction equation

[N:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=2[NH:3][CH:2]=1.[Cl:11][C:12]1[CH:22]=[CH:21][C:15]2[S:16][CH:17]=[C:18]([CH2:19]Br)[C:14]=2[CH:13]=1.C([O-])([O-])=O.[K+].[K+]>>[Cl:11][C:12]1[CH:22]=[CH:21][C:15]2[S:16][CH:17]=[C:18]([CH2:19][N:10]([CH2:19][C:18]3[C:14]4[CH:13]=[C:12]([Cl:11])[CH:22]=[CH:21][C:15]=4[S:16][CH:17]=3)[C:8]3[CH:7]=[CH:6][C:5]4[NH:1][CH:2]=[N:3][C:4]=4[CH:9]=3)[C:14]=2[CH:13]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 136235-Aminobenzimidazole

HCID 27798573-(Bromomethyl)-5-chloro-1-benzothiophene

Product 1

HCID 178477921N,N-Bis((5-chlorobenzo[b]thiophen-3-yl)methyl)-1H-benzo[d]imidazol-5-amine

Procedure

The compound was synthesized starting from benzimidazol-5-amine (133 mg; 1 mmol; 1 eq.), (5-chlorobenzo[b]thiophen-3-yl)methylbromide (576 mg; 2.2 mmol; 2.2 eq.) and K2CO3 (304 mg; 2.2 mmol; 2.2 eq.) according to method 5; Yield: 0.187 g (37.9%); MS m/z: 494.4/496.5 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 4.84 (s, 4H); 6.90-6.92 (m, 2H); 7.37-7.39 (m, 3H); 7.51 (s, 2H); 7.88 (d, 2H); 7.94-7.96 (m, 2H); 7.98 (s, 1H); 12.00 (br s, 1H); HPLC (METHOD [A]): rt 19.77 min (100%)

Workup

customThe compound was synthesized
customrt 19.77 min (100%)

Sources & evidence

ORD record: ord-08e7f3551d9f4fa4a12232080709da1d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541596B2

Reaction notes

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