Ethanolamine → HCID 86717869, compound

HRID 2281024Notes

Reaction equation

HRID 2281024 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1C)[CH:5]=O.[Cl-].[Ca+2].[Cl-].[CH2:14]([CH2:16][NH2:17])[OH:15].C1(C)C=CC(S([CH:27]([N+:38]#[C-:39])[C:28]2[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[CH:29]=2)(=O)=O)=CC=1.C(N)(C)(C)C.C1C[O:49][CH2:48]C1>C(O)C.ClCCl>[OH:15][CH2:14][CH2:16][N:17]1[C:5]([C:4]2[CH:7]=[CH:8][C:9]([O:49][CH3:48])=[C:2]([F:1])[CH:3]=2)=[C:27]([C:28]2[CH:29]=[C:30]([O:36][CH3:37])[CH:31]=[C:32]([O:34][CH3:35])[CH:33]=2)[N:38]=[CH:39]1

Participants

9

Reactant 6

HCID 700EthanolamineHCID 6385Tert-ButylamineHCID 8028TetrahydrofuranHCID 27745743-Fluoro-4-methylbenzaldehydeHCID 5284359Calcium ChlorideHCID 86717870HCID 86717870, compound

Product 1

HCID 86717869HCID 86717869, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-Fluoro-4-methylbenzaldehyde (1.0 g, 6.49 mmol) and 30 mL anhydrous dichloromethane were added into a 100 mL three-necked flask and dissolved with stirring Anhydrous calcium chloride (6.0 g) and ethanolamine (1.7 g) were added, and the reaction lasted for 3-4 days at room temperature. The solid was filtered off, and the filtrate was concentrated under reduced pressure to obtain a light yellow solid residue. The residue was dissolved by adding 50 mL anhydrous ethanol. Then, 1-p-toluenesulfonyl-1-(3,5-dimethoxyphenyl) methyl isonitrile 2.6 g (8 mmol) and anhydrous THF (40 mL), tert-butylamine (2.4 mL) were added in succession, and the reaction lasted at 25-35° C. for 40 hours with stirring. The mixture was concentrated under reduced pressure, and the residue was washed by addition of 40 mL ethyl acetate, filtered and dried by suction to give a pale yellow solid, which was further purified by silica gel column chromatography (ethyl acetate:methanol=25:1) to afford the desired compound, as a white solid. Melting point: 202˜204° C.

Workup

  1. additionwere added
  2. filtrationThe solid was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customto obtain a light yellow solid residue
  5. dissolutionThe residue was dissolved
  6. waitthe reaction lasted at 25-35° C. for 40 hours
  7. concentrationThe mixture was concentrated under reduced pressure
  8. washthe residue was washed by addition of 40 mL ethyl acetate
  9. filtrationfiltered
  10. customdried by suction
  11. customto give a pale yellow solid, which
  12. customwas further purified by silica gel column chromatography (ethyl acetate:methanol=25:1)

Sources & evidence

ORD record
ord-bf97d64cb1474216b186c8a090b27f4b
Source dataset
uspto-grants-2015_09
Patent number
US09139574B2

Reaction notes

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