Hydrochloric Acid → HCID 15023454, compound

HRID 973997Notes

Reaction equation

HRID 973997 reaction equation
[CH2:1]([NH:4][C:5](=[O:20])[C:6]([OH:19])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:2]#[CH:3].[CH2:21]=[O:22].Cl.[Cl-].[Na+]>CS(C)=O.C(=O)([O-])[O-].[K+].[K+]>[OH:22][CH2:21][C:3]#[C:2][CH2:1][NH:4][C:5](=[O:20])[C:6]([OH:19])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5234Sodium ChlorideHCID 15023456HCID 15023456, compound

Product 1

HCID 15023454HCID 15023454, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of N-(2-propynyl)-2-hydroxy-2,2-diphenylacetamide (165.2 g), cuprous chloride (2.50 g) and potassium carbonate (1.73 g) in dimethylsulfoxide (330 ml) was stirred at 75° C. for 45 minutes under a nitrogen atmosphere. To the reaction mixture was added paraformaldehyde (25.3 g) and the mixture was stirred at 85° C. for 5 hours. The reaction mixture was poured into the mixture of 5% hydrochloric acid and 10% aqueous solution of sodium chloride (1:5), and extracted with ethyl acetate. The extracts were washed successively with brine, 5% aqueous solution of sodium thiosulfate and brine, dried over magnesium sulfate and evaporated in vacuo. To the residue was added a mixture of diisopropyl ether and chloroform (1:1) (100 ml) and the mixture was stirred at room temperature for 30 minutes. The resulting precipitates were collected by filtration, washed with a mixture of diisopropyl ether and chloroform (1:1) and dried to give N-(4-hydroxy-2-butynyl)-2-hydroxy-2,2-diphenylacetamide (119.7 g).

Workup

  1. stirringthe mixture was stirred at 85° C. for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed successively with brine, 5% aqueous solution of sodium thiosulfate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. additionTo the residue was added
  7. additiona mixture of diisopropyl ether and chloroform (1:1) (100 ml)
  8. stirringthe mixture was stirred at room temperature for 30 minutes
  9. customThe resulting precipitates
  10. filtrationwere collected by filtration
  11. washwashed with a mixture of diisopropyl ether and chloroform (1:1)
  12. customdried

Sources & evidence

ORD record
ord-77c209a9134347be8b4ae336b0f23a0e
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Reaction notes

Loading…