Cyanogen Bromide → HCID 10926720, compound

HRID 650039Notes

Reaction equation

HRID 650039 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([NH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:10][NH2:11])[CH:7]=1.[N:24]#[C:25]Br.C(=O)(O)[O-].[Na+].[K+].[Br-]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([N:8]2[C:9]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:17]=3)=[N:10][N:11]=[C:25]2[NH2:24])[CH:7]=1

Participants

7

Reactant 4

HCID 10476Cyanogen BromideHCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 178490717HCID 178490717, compound

Product 1

HCID 10926720HCID 10926720, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(5-Chloro-2-methoxyphenyl)-4-(trifluoromethyl)benzene carbohydrazonamide (1.5 g, 4.36 mmol) was dissolved in 1,4-dioxane (7 ml) and cyanogen bromide (475 mg, 4.48 mmol) was added. A solution of sodium bicarbonate (380 mg in 7 ml of water) was added dropise at room temperature and the reaction mixture was stirred for 3 h. An additional 7 ml of water was added to the heterogenous reaction mixture before filtration and rinse with water. Recrystallization from acetonitrile gave 922 mg (57.3%) mp 247-248° C.; IR(KBr, υ=cm−1) 3416, 3076, 3052, 1652, 1561, 1504, 1322, 1110; 1 H NMR (300 MHz, DMSO-d6) δ 3.60 (3H, s), 5.92 (2H, s), 7.22 (1H, d, J=9.5 Hz), 7.47 (2H, d, 8.3 Hz), 7.54-7.57 (2H, m), 7.67 (1H, d, J=8.4 Hz).; MS(DCl)m/z: 369(MH+). Anal. calcd. for C16H12ClF3N4O: C, 52.12; H, 3.28; N, 15.19. Found: C, 52.19; H, 3.20; N, 15.29.

Workup

  1. washrinse with water
  2. customRecrystallization from acetonitrile
  3. customgave 922 mg (57.3%) mp 247-248° C.

Sources & evidence

ORD record
ord-f560a5700ed84635b9df48862bbfa676
Source dataset
uspto-grants-2001_08
Patent number
US06271249B1

Reaction notes

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