Triethylamine → HCID 13630889, compound

HRID 1981463Notes

Reaction equation

HRID 1981463 reaction equation
BrBr.[Cl:3][C:4]1[CH:5]=[C:6]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[C:7](C(N)C#N)=[O:8].[CH2:17]([OH:21])[C:18]#[C:19][CH3:20].Br.C([N:25](CC)[CH2:26][CH3:27])C.C([N:32](CC)CC)C>C(OCC)(=O)C.O.O1CCCC1>[CH2:17]([O:21][CH:27]([NH:32][C:7](=[O:8])[C:6]1[CH:13]=[C:14]([Cl:16])[CH:15]=[C:4]([Cl:3])[CH:5]=1)[C:26]#[N:25])[C:18]#[C:19][CH3:20]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 129912-Butyn-1-olHCID 24408Bromine3×HCID 2734074Triethylammonium bromideHCID 53975759HCID 53975759, compound

Product 1

HCID 13630889HCID 13630889, compoundYield 79.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Bromine (2.8 g) was added at a time to a solution of 4.0 g of 3,5-dichlorobenzoyl aminoacetonitrile in 100 ml of ethyl acetate at room temperature. The mixture was stirred until the color of bromine in the reaction solution disappeared. The reaction solution was then cooled to 0° to 5° C. A mixture of 1.5 g of 2-butyn-1-ol, 3.5 g of triethylamine and 30 ml of tetrahydrofuran was cooled to 0° to 5° C. on an ice bath, and with stirring, the ethyl acetate solution of the bromine compound prepared above was added dropwise. After the addition, the reaction was continued for 30 minutes under cooling. Water (100 ml) was added to dissolve the precipitated triethylamine hydrobromide. The oil layer was separated, washed with water, and dried. The solvent was then distilled off under reduced pressure. The residual solid was suspended in ethyl ether, filtered, washed and dried to give 4.2 g of the desired alpha-(2-butynyloxy)-3,5-dichlorobenzoylaminoacetonitrile as a white solid. The yield was 79.9%, and the melting point of the product was 124° to 128° C.

Workup

  1. temperatureThe reaction solution was then cooled to 0° to 5° C
  2. temperaturewas cooled to 0° to 5° C. on an ice bath
  3. additionabove was added dropwise
  4. additionAfter the addition
  5. temperatureunder cooling
  6. customThe oil layer was separated
  7. washwashed with water
  8. customdried
  9. distillationThe solvent was then distilled off under reduced pressure
  10. filtrationfiltered
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-d7c859fd74504513832704ae49051196
Source dataset
uspto-grants-1986_06
Patent number
US04592773

Reaction notes

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