Ammonia → HCID 14234831, compound

HRID 1607139Notes

Reaction equation

HRID 1607139 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Cl)(Cl)Cl.Cl[CH2:13][C:14]#[N:15].[Cl-:16].[Al+3].[Cl-].[Cl-].Cl.N.[OH2:22]>C(Cl)Cl>[C:14]([NH:15][CH:4]1[CH2:5][CH2:6][C:4]2[C:3](=[CH:2][C:1]([OH:7])=[C:6]([C:1](=[O:7])[CH2:2][Cl:16])[CH:5]=2)[CH2:3]1)(=[O:22])[CH3:13]

Participants

9

Reactant 7

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962Water2×HCID 996PhenolHCID 7856ChloroacetonitrileHCID 25135Boron TrichlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14234831HCID 14234831, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

5 g of the phenol obtained in the preceding stage, suspended in methylene chloride, are added to 58 ml of a molar solution of boron trichloride in methylene chloride. 4.4 g of chloroacetonitrile are then added followed, portionwise, by 3.69 g of aluminum chloride, the temperature being maintained in the region of 0° C. The mixture is left stirred for 4 hours at 0° C. and then left overnight at room temperature, and it is then hydrolyzed with 15 ml of water and 27 ml of 10% strength aqueous hydrochloric acid solution. This mixture is left for 1 hour with stirring and then alkalinized with 20% strength ammonia solution in water. The precipitate obtained is filtered off on celite, followed by washing with methylene chloride, the two phases are separated after settling has occurred and the organic phase is dried over anhydrous magnesium sulfate. After evaporation of the solvent, the residue is recrystallized in ethanol.

Workup

  1. waitThe mixture is left
  2. waitleft overnight at room temperature
  3. waitThis mixture is left for 1 hour
  4. stirringwith stirring
  5. customThe precipitate obtained
  6. filtrationis filtered off on celite
  7. washby washing with methylene chloride
  8. customthe two phases are separated after settling
  9. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  10. customAfter evaporation of the solvent
  11. customthe residue is recrystallized in ethanol

Sources & evidence

ORD record
ord-3486e97b951f461080945163f5be6e94
Source dataset
uspto-grants-1989_09
Patent number
US04863951

Reaction notes

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