Dimethylformamide → HCID 1648919, compound

HRID 1752812Notes

Reaction equation

HRID 1752812 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.[NH2:12][C:13]1[N:17]=[C:16]([SH:18])[NH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][S:18][C:16]2[N:17]=[C:13]([NH2:12])[NH:14][N:15]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 1785092965-amino-1H-1,2,4-triazole-3-thiol

Product 1

HCID 1648919HCID 1648919, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(2-bromoethoxy)-4-chlorobenzene (2.0 g, 8.49 mmol), 3-amino-5-mercapto-1,2,4-triazole (1.04 g, 8.92 mmol), potassium carbonate (2.34 g, 16.98 mmol), and anhydrous N,N-dimethylformamide (4 mL) was added to a 50 mL RBF with a magnetic stirring bar. The mixture was allowed to stir at ambient temperature for 3 days. Progress of the reaction was monitored by analytical HPLC with UV detection at 215 nm (Rt=6.04 min). The mixture was diluted with 40 mL of water and allowed to stir for 5 min. A precipitate was isolated by filtration, rinsed with 25 mL of water, and allowed to dry under reduced pressure. The solid material was >98% pure by analytical HPLC and afforded the title compound as a white powder (2.21 g, 96% yield). EM (calc.): 270.7; MS (ESI) m/e: 271.0 (M+H)+. 1H NMR (DMSO-d6, 400 MHz) δ ppm: 12.00 (br s, 1H), 7.32 (d, 2H), 7.00 (d, 2H), 6.04 (s, 2H), 4.19 (t, 2H), 3.30 (t, 2H).

Workup

  1. additionwas added to a 50 mL RBF with a magnetic stirring bar
  2. stirringto stir for 5 min
  3. customA precipitate was isolated by filtration
  4. washrinsed with 25 mL of water
  5. customto dry under reduced pressure

Sources & evidence

ORD record
ord-1c887adfd0dc4f9ab8d62133c9298a8b
Source dataset
uspto-grants-2015_10
Patent number
US09163027B2

Reaction notes

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