Ammonia → HCID 69476210, compound

HRID 1294575Notes

Reaction equation

HRID 1294575 reaction equation
[CH3:1][C:2]1([CH3:18])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1.[F:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].C[Si]([C:31]#[N:32])(C)C.N>C(O)(=O)C>[CH3:1][C:2]1([CH3:18])[CH:7]2[CH2:8][CH:3]1[CH2:4][CH2:5][CH:6]2[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][C:14]([NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:20]([F:19])[CH:21]=2)([C:31]#[N:32])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 97423-FluoroanilineHCID 82115Trimethylsilyl cyanideHCID 58906455HCID 58906455, compound

Product 1

HCID 69476210HCID 69476210, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 20.0 g (80.2 mmol) of (26) and 8.4 ml (87 mmol) of 3-fluoroaniline (27a) in 65 ml of acetic acid was cooled with a cold water bath. 10.7 ml (80.2 mmol) of trimethylsilylcyanide were added dropwise over a period of 10 min. maintaining the temperature below 40° C. The mixture was stirred for 2 h at room temperature and poured into a mixture of aqueous ammonia (80 ml) and ice (80 g). The pH was adjusted to 10 with concentrated NH3. The mixture was extracted with chloroform (3×200 ml). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to give 40.0 g of crude product, which was purified by column chromatography (SiO2, heptane:EtOAc, 1:1) to give 28.7 g (77.7 mmol, 97%) of (28a). It is also possible to use crude product in the next step without purification.

Workup

  1. temperaturemaintaining the temperature below 40° C
  2. extractionThe mixture was extracted with chloroform (3×200 ml)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give 40.0 g of crude product, which
  6. customwas purified by column chromatography (SiO2, heptane:EtOAc, 1:1)

Sources & evidence

ORD record
ord-a9684eafa89f4e9193c6caa0f69366c0
Source dataset
uspto-grants-2007_07
Patent number
US07241770B2

Reaction notes

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