Benzoyl chloride → HCID 54125572, compound

HRID 1981408Notes

Reaction equation

HRID 1981408 reaction equation
Cl.[NH2:2][C@@H:3]([CH3:8])[C:4](=[O:7])[CH2:5][Cl:6].[C:9](Cl)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:9]([NH:2][C@@H:3]([CH3:8])[C:4](=[O:7])[CH2:5][Cl:6])(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 91654124HCID 91654124, compound

Product 1

HCID 54125572HCID 54125572, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a vigorously stirred suspension of (S)-3-amino-1-chloro-2-butanone, monohydrochloride (3.0 g., 19.0 mmole) in 150 ml. of tetrahydrofuran at 0°-5° is added, sequentially, benzoyl chloride (2.2 ml., 19.0 mmole), triethylamine (2.65 ml., 19.0 mmole), and sodium bicarbonate (1.6 g., 19.0 mmole). The reaction mixture is stirred for 15 minutes in the cold and then for 2 hours at room temperature. The solvent is evaporated and the residue is partitioned between ethyl acetate (400 ml.) and ice-water (40 ml.). The organic layer is washed with 5% potassium bisulfate (2×30 ml.) and water (3×30 ml.), then dried and evaporated. The resulting crystalline residue is recrystallized from benzene-petroleum ether giving three crops of comparable purity totaling 3.67 g.; m.p. 119.5°-121.5° (first crop), 118°-119.5° (third crop). A portion is recrystallized once more giving an analytically pure sample of (S)-3-(benzoylamino)-1-chloro-2-butanone; m.p. 119.5°-121°.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between ethyl acetate (400 ml.) and ice-water (40 ml.)
  3. washThe organic layer is washed with 5% potassium bisulfate (2×30 ml.) and water (3×30 ml.)
  4. customdried
  5. customevaporated
  6. customThe resulting crystalline residue is recrystallized from benzene-petroleum ether giving three crops of comparable purity
  7. customm.p. 119.5°-121.5° (first crop), 118°-119.5° (third crop)
  8. customA portion is recrystallized once more

Sources & evidence

ORD record
ord-fafa077a700142d99005859b342726a4
Source dataset
uspto-grants-1985_04
Patent number
US04514391

Reaction notes

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