Water → HCID 57144140, compound

HRID 861416Notes

Reaction equation

HRID 861416 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.C(=O)([O-])[O-:16].[Na+].[Na+].O>C(OCC)(=O)C>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([C:3]#[C:2][C:1]([NH2:4])=[O:16])=[O:11])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 685154-Bromobenzoyl chlorideHCID 239041Propargylamine

Product 1

HCID 57144140HCID 57144140, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of propargylamine (3.55 g) in ethyl acetate (25 ml) was added over a period of 15 minutes to a stirred mixture of 4-bromobenzoyl chloride (14.2 g) and sodium carbonate (10.6 g) in ethyl acetate (100 ml) at ambient temperature. The mixture was heated at reflux for 1 hour. The mixture was cooled to ambient temperature and water (200 ml) was added. The mixture extracted with ethyl acetate (2×100 ml). The ethyl acetate extracts were combined, washed with saturated aqueous sodium bicarbonate solution, saturated with brine, dried (MgSO4) and evaporated. The solid residue was recrystallised from ethyl acetate to give 4-bromobenzoyl propargyl amide (8.9 g), m.p. 281°-288° C.; NMR: 3.10(1H,m), 4.05(2H,m), 7.69(2H,m), 7.80(2H,m), 9.0(1H,m); m/z 238(M+H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. extractionThe mixture extracted with ethyl acetate (2×100 ml)
  4. washwashed with saturated aqueous sodium bicarbonate solution, saturated with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe solid residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-d9a44e5193024559911c3c6cb24ba51c
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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