Ammonium Chloride → HCID 86681249, compound

HRID 1848274Notes

Reaction equation

HRID 1848274 reaction equation
[CH3:1][S:2][C:3]1[S:4][C:5]2[CH:11]=[C:10]([CH2:12][N:13]3[C:17]4[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:16]=4[N:15]=[CH:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+]>CN(C=O)C>[N:23]1[NH:24][N:25]=[N:26][C:22]=1[C:20]1[CH:19]=[CH:18][C:17]2[N:13]([CH2:12][C:10]3[CH:9]=[CH:8][C:6]4[N:7]=[C:3]([S:2][CH3:1])[S:4][C:5]=4[CH:11]=3)[CH:14]=[N:15][C:16]=2[CH:21]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86681247HCID 86681247, compound

Product 1

HCID 86681249HCID 86681249, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A suspension of 1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (694 mg, 2.1 mmol), sodium azide (403 mg, 6.3 mmol), and ammonium chloride (331 mg, 6.3 mmol) in DMF (3 mL) was heated in a sealed tube at 125° C. for 15 h. The mixture was cooled to rt and a precipitate formed. The solid was collected by filtration to afford 6-((5-(2H-tetrazol-5-yl)-1H-benzo[d]imidazol-1-yl)methyl)-2-(methylthio)benzo[d]thiazole (796 mg, 100%) as a yellow solid that did not require further purification. 1H NMR (500 MHz, DMSO-d6) δ 8.41 (s, 1H), 8.19 (s, 1H), 8.02 (s, 1H), 7.88 (dd, J=1.0, 8.4 Hz, 1H), 7.81 (d, J=8.6 Hz, 1H), 7.52 (d, J=8.4 Hz, 1H), 7.45 (dd, J=1.4, 8.5 Hz, 1H), 7.15-7.30 (br s, 2H), 5.60 (s, 2H), 2.76 (s, 3H); LCMS (ESI) m/z 380 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customa precipitate formed
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-859d9a3a883145728590eb63858572eb
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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