Hydrochloric Acid → HCID 89717682, compound

HRID 930199Notes

Reaction equation

HRID 930199 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[H-].[Na+].[H][H].F[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:19]=[N:20][N:21]([CH3:23])[N:22]=2)=[CH:14][C:13]=1[N+:24]([O-:26])=[O:25].Cl>CN(C=O)C>[C:1]([CH:3]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:19]=[N:20][N:21]([CH3:23])[N:22]=2)=[CH:14][C:13]=1[N+:24]([O-:26])=[O:25])[C:4]([NH2:6])=[O:5])#[N:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 89717655HCID 89717655, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89717682HCID 89717682, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 2-cyanoacetamide (0.888 g, 10.56 mmol) in DMF (2.268 mL) was added to a suspension of sodium hydride 60% wt. in mineral oil (0.443 g, 11.08 mmol) in DMF (5.67 mL) to give a grey suspension. After cooling to 0° C. (Note: Hydrogen Gas evolution) the resulting mixture was stirred at 0° C. for 30 minutes. Then a solution of 5-(4-fluoro-3-nitrophenyl)-2-methyl-2H-tetrazole (1.15 g, 5.15 mmol) in DMF (2.3 mL) was added to give a deep purple solution. After 3 hours, the reaction mixture was slowly poured into an ice-water mixture (33.0 mL) and conc.HCl (0.952 mL). The resulting yellow slurry was stirred for 30 minutes, the solid was filtered, washed with water (3×5 mL) and then with Hexane (2×5 mL), dried at 40° C. under high vacuum until constant weight to give 2-cyano-2-(4-(2-methyl-2H-tetrazol-5-yl)-2-nitrophenyl)acetamide (1.41 g, 95% yield) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 4.49 (s, 3H) 5.77 (s, 1H) 7.77 (s, 1H) 7.95 (d, J=8.2 Hz, 1H) 8.03 (s, 1H) 8.51 (dd, J=8.2, 1.8 Hz, 1H) 8.70 (d, J=1.8 Hz, 1H); MS m/z 288.1 (M+H)+; HPLC 96.4% @ 220 nm, RT=1.31 minutes.

Workup

  1. customto give a grey suspension
  2. customto give a deep purple solution
  3. waitAfter 3 hours
  4. stirringThe resulting yellow slurry was stirred for 30 minutes
  5. filtrationthe solid was filtered
  6. washwashed with water (3×5 mL)
  7. dry with materialwith Hexane (2×5 mL), dried at 40° C. under high vacuum until constant weight

Sources & evidence

ORD record
ord-de41c17b549f45f98d0798b3dfc4a6e0
Source dataset
uspto-grants-2016_03
Patent number
US09296744B2

Reaction notes

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