Ammonia → HCID 16790478, compound

HRID 1832153Notes

Reaction equation

HRID 1832153 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=O.[NH3:11].C[Si]([C:16]#[N:17])(C)C.CCCCCC.CCOC(C)=O>CO>[NH2:11][CH:5]([C:4]1[CH:7]=[CH:8][C:9]([F:10])=[C:2]([F:1])[CH:3]=1)[C:16]#[N:17]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 82115Trimethylsilyl cyanideHCID 5880883,4-DifluorobenzaldehydeHCID 21226206Ethyl acetate hexane

Product 1

HCID 16790478HCID 16790478, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Through a solution of 3,4-difluorobenzaldehyde (25.0 g, 0.176 mol) in MeOH (500 mL) in a round bottom flask, was bubbled ammonia gas for two hours at room temperature. The flask was then cooled to 0° C. and trimethylsilyl cyanide was then added slowly. The reaction mixture was stirred for 2 h, at which time TLC analysis indicated that the reaction was complete (Rf=0.35, 3:2 hexane/EtOAc). The solvent was removed in vacuo and the residue was subjected to flash column chromatography on silica gel to obtain the desired product, which was used in the next step without purification.

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-eab7bdc8c0f24c49a251975804bdd07d
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

Loading…