Cyanogen Bromide → HCID 9932309, compound

HRID 1265165Notes

Reaction equation

HRID 1265165 reaction equation
[F:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[CH3:21])=[C:4]([CH:9]=[CH:10][C:11]=1[F:12])[C:5]([NH:7][NH2:8])=[O:6].[N:22]#[C:23]Br.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[C:3]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([I:20])=[CH:16][C:15]=2[CH3:21])=[C:4]([C:5]2[O:6][C:23]([NH2:22])=[N:8][N:7]=2)[CH:9]=[CH:10][C:11]=1[F:12]

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 12045116HCID 12045116, compound

Product 1

HCID 9932309HCID 9932309, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3,4-Difluoro-2-(4-iodo-2-methyl-phenylamino)-benzoic acid hydrazide (0.806 g, 2 mmol) in 5 ml of dioxane was added cyanogen bromide (0.212 g, 2 mmol) followed by a solution of sodium bicarbonate (0.17 g, 2 mmol) in 5 ml of water. The resulting mixture was stirred 18 ours at room temperature. The solution was concentrated and the residure was run column with hexanes/ethyl acetate (3/1) to give the product which was recrystallized from ethyl acetate/hexanes to provide a pale-yellow crystal. The yield: 58% m.p. 183.7-184.0° C. 1H NMR(CDCl3, 400 Hz): /ppm 8.87(1H, s, —NH—); 7.52(1H, s, Phenyl-H); 7.45-7.49(1H, m, Phenyl-H); 7.40(1H, d, J=8.3 Hz, Phenyl-H); 6.77-6.83(1H, m Phenyl-H); 6.60-6.63(1H, m, Phenyl-H); 5.02(2H, s, —NH2), 2.36(3H, s, CH3)

Workup

  1. concentrationThe solution was concentrated
  2. customto give the product which
  3. customwas recrystallized from ethyl acetate/hexanes
  4. customto provide a pale-yellow crystal

Sources & evidence

ORD record
ord-906e8f5ac21047e9ad16d3b66e602835
Source dataset
uspto-grants-2003_04
Patent number
US06545030B1

Reaction notes

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