Benzaldehyde → HCID 12597218, compound

HRID 441062Notes

Reaction equation

HRID 441062 reaction equation
S(=O)(O)[O-].[Na+].[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[C-:21]#[N:22].[K+]>O.CO.O.CO>[CH:14]1([NH:20][CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:21]#[N:22])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 7965CyclohexylamineHCID 9032Potassium CyanideHCID 23665763Sodium Bisulfite

Product 1

HCID 12597218HCID 12597218, compoundYield 79.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 0.98 g (9.4 mmol) of sodium bisulfite in 4 ml of water was treated with 0.96 ml (9.4 mmol) benzaldehyde in 5 ml of methanol. The resulting mixture was cooled to 5°-10° C. and treated with cyclohexylamine, whereupon a thick precipitate was formed. With the reaction mixture still at approximately 5° C., solid potassium cyanide (0.61 g, 9.4 mmol) was added portionwise over 2 minutes. The precipitate became thick enough to halt stirring and 5 ml of 1:1 methanol water was added to facilitate stirring. The reaction mixture was allowed to warm to room temperature over a 16 hour period. The mixture was then filtered and the product was washed with methanol-water and dried in air. There were obtained 1.6 grams (79.6% yield) of the above titled product. 1H NMR (300 MHz, CDCl3) δ7.5-7.3 (m, 5H), 4.82 (s, 1H), 2.9-2.8 (m, 1H), 2.0 (d, 1H, J=12 Hz), 1.75-1.62 (m, 4H), 1.4-1.0 (m, 6H). 13C NMR (75 MHz, CDCl3) δ135.56, 128.99, 128.91, 127.29, 119.35, 54.87, 51.68, 33.87, 31.94, 25.95, 24.66, 24.27. IR CHCl3 λ 2220 cm-1. Mass Spectrum m/e 214 p+.

Workup

  1. temperatureThe resulting mixture was cooled to 5°-10° C.
  2. customwas formed
  3. stirringto facilitate stirring
  4. filtrationThe mixture was then filtered
  5. washthe product was washed with methanol-water
  6. customdried in air

Sources & evidence

ORD record
ord-135fad272c9c4a9fbd57a9dffa2564fd
Source dataset
uspto-grants-1996_05
Patent number
US05521220

Reaction notes

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