Sodium Cyanide → HCID 59402933, compound

HRID 538508Notes

Reaction equation

HRID 538508 reaction equation
[C-:1]#[N:2].[Na+].CC1C=CC(S(O[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([NH2:33])=[O:32])[CH:26]=2)(=O)=O)=CC=1>O.CCO>[C:1]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[C:27]([C:31]([NH2:33])=[O:32])[CH:28]=[CH:29][CH:30]=1)#[N:2]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 59402852HCID 59402852, compound

Product 1

HCID 59402933HCID 59402933, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
75 °C

Procedure

Sodium cyanide (60 mg, 1.22 mmol, 1.3 equiv.) was added to a solution of 9-[3-(aminocarbonyl)phenoxy]nonyl 4-methylbenzenesulfonate (407 mg, 0.94 mmol, 1 equiv.) in water (10 ml) and 95% EtOH (8 ml), and the reaction mixture was stirred at 75° C. for 2 days. After cooling at r.t., the mixture was diluted with water (10 ml) and extracted with CH2Cl2 (3×10 ml). The combined organic extracts were dried (MgSO4) and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography on silica eluting with EtOAc/hexane (50%), to give the desired compound as white solid (57 mg, 21%), mp 96-97° C. HPLC-MS (method 1): m/z 289 [M+H]+, Rt=4.16 min.

Workup

  1. temperatureAfter cooling at r.t.
  2. extractionextracted with CH2Cl2 (3×10 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. customthe solvent was removed under reduced pressure
  5. customThe crude residue was purified by column chromatography on silica eluting with EtOAc/hexane (50%)

Sources & evidence

ORD record
ord-88aa3cfb919d467d80c11290d75416fb
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

Loading…