Potassium Carbonate → N-(4-Ethylbenzyl)-N-((benzo[d]thiazol-2-yl)methyl)-1H-benzo[d]imidazol-5-amine

HRID 45963Notes

Reaction equation

HRID 45963 reaction equation
[CH2:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][NH:8][C:9]2[CH:17]=[CH:16][C:12]3[N:13]=[CH:14][NH:15][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[S:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:21]1[CH2:29]Br.C([O-])([O-])=O.[K+].[K+]>>[CH2:1]([C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]([CH2:29][C:21]2[S:20][C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[N:22]=2)[C:9]2[CH:17]=[CH:16][C:12]3[NH:13][CH:14]=[N:15][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 27762582-(Bromomethyl)-1,3-benzothiazoleHCID 67443948N-(4-Ethylbenzyl)-1H-benzo[d]imidazol-5-amine

Product 1

HCID 178436369N-(4-Ethylbenzyl)-N-((benzo[d]thiazol-2-yl)methyl)-1H-benzo[d]imidazol-5-amine

Procedure

The compound was synthesized starting from N-(4-ethylbenzyl)benzimidazol-5-amine (251 mg; 1 mmol; 1 eq.), (benzo[d]-thiazol-2-yl)methylbromide (251 mg; 1.1 mmol; 1.1 eq.) and K2CO3 (152 mg; 1.1 mmol; 1.1 eq.) according to method 6; Yield: 0.118 g (29.6%);; MS m/z: 399.4 [M+H]+; 1H-NMR (500 MHz, DMSO d6): δ 1.14 (t, 3H, 3J=7.6 Hz); 2.56 (q, 2H, 3J=7.6 Hz); 4.74 (s, 2H); 5.02 (s, 2H); 6.85-6.86 (m, 2H); 7.15-7.17 (m, 2H); 7.26-7.27 (m, 2H); 7.36-7.39 (m, 2H); 7.46-7.49 (m, 1H); 7.94-7.95 (m, 2H), 7.98-8.00 (m, 1H); 11.98 (br s, 1H); HPLC (METHOD [A]): rt 17.02 min (97.8%)

Workup

  1. customThe compound was synthesized
  2. customrt 17.02 min (97.8%)

Sources & evidence

ORD record
ord-6d104f953ae4490796001a36d84d62e5
Source dataset
uspto-grants-2013_09
Patent number
US08541596B2

Reaction notes

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