Ammonia → 5-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)-1H-benzo[d]imidazole-2(3H)-thione

HRID 578186Notes

Reaction equation

HRID 578186 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[CH:7][C:5]=2[N:6]=1.O[N:15]=[C:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1.N>>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]2[N:23]=[C:11]([C:9]3[CH:8]=[CH:7][C:5]4[NH:6][C:2](=[S:1])[NH:3][C:4]=4[CH:10]=3)[O:13][N:15]=2)[CH:18]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 308113N-HydroxynicotinimidamideHCID 178524147HCID 178524147, compound

Product 1

HCID 445450715-(3-(pyridin-3-yl)-1,2,4-oxadiazol-5-yl)-1H-benzo[d]imidazole-2(3H)-thione

Procedure

The title compound was prepared according to Method C using 2-mercapto-5-benzimidazolecarboxylic acid (Princeton) and N′-hydroxynicotinimidamide (Tyger). 1H NMR (300 MHz, CD3OD) δ 7.38 (d, J=8.5 Hz, 1H), 7.65 (ddd, J=8.0, 4.9, 0.7 Hz, 1H), 7.86 (d, J=1.0 Hz, 1H), 8.00 (dd, J=8.1, 1.7 Hz, 1H), 8.45 (dt, J=8.0, 1.9 Hz, 1H), 8.81 (dd, J=4.9, 1.5 Hz, 1H), 9.26 (dd, J=2.2, 0.9 Hz, 1H) ppm; MS (DCI/NH3) m/z 296 (M+H)+.

Sources & evidence

ORD record
ord-8b38ff87bebe4b56b2694d6cc365fd8e
Source dataset
uspto-grants-2015_05
Patent number
US09040568B2

Reaction notes

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