Chloroform → 2-bromo-N-(4-oxo-1-benzopyran-3-yl)-acetamide

HRID 2057890Notes

Reaction equation

HRID 2057890 reaction equation
C(Cl)(Cl)Cl.[NH2:5][C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:8][CH:7]=1.C(N(CC)C(C)C)(C)C.[Br:26][CH2:27][C:28](Cl)=[O:29]>C1(C)C=CC=CC=1>[Br:26][CH2:27][C:28]([NH:5][C:6]1[C:15](=[O:16])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:8][CH:7]=1)=[O:29]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 122586463-Aminochromone

Product 1

HCID 205422152-bromo-N-(4-oxo-1-benzopyran-3-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

10 ml of chloroform are added to 8 g of 3-aminochromone in 200 ml of toluene and the mixture is warmed to 40° C. After cooling to 20° C., 10 ml of N,N-diisopropylethylamine are added with stirring, followed by the addition of 4.8 ml of bromoacetyl chloride in 20 ml of toluene at 10° C. in the course of 5 minutes. When the addition is complete, the reaction mixture is stirred for 1 hour at room temperature. The crystalline precipitate which has formed is collected by suction, washed with water and recrystallised from ethanol/petroleum ether, yielding 11.8 g of 2-bromo-N-(4-oxo-1-benzopyran-3-yl)-acetamide with a melting point of 198° C.

Workup

  1. temperatureAfter cooling to 20° C.
  2. additionWhen the addition
  3. stirringthe reaction mixture is stirred for 1 hour at room temperature
  4. customThe crystalline precipitate which has formed
  5. customis collected by suction
  6. washwashed with water
  7. customrecrystallised from ethanol/petroleum ether

Sources & evidence

ORD record
ord-1862af8d3b1643eaa6114f456b45a01c
Source dataset
uspto-grants-1980_07
Patent number
US04213980

Reaction notes

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