Chloroacetyl chloride → HCID 86722014, compound

HRID 524985Notes

Reaction equation

HRID 524985 reaction equation
[NH2:1][N:2]1[CH:6]=[CH:5][C:4]([Cl:7])=[C:3]1[C:8]([OH:10])=[O:9].[Cl:11][CH2:12][C:13](Cl)=[O:14]>C(O)(=O)C>[Cl:7][C:4]1[CH:5]=[CH:6][N:2]([NH:1][C:13](=[O:14])[CH2:12][Cl:11])[C:3]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 22180015HCID 22180015, compound

Product 1

HCID 86722014HCID 86722014, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1-amino-3-chloro-1H-pyrrole-2-carboxylic acid (12.51 g, 55% purity, 0.04 mol) in 500 mL of glacial acetic acid were added under argon 17 mL of chloroacetyl chloride (0.21 mol) and the mixture was stirred at room temperature during 1.5 hours. Afterwards, the reaction mixture was poured into ice-water and extracted with ethyl acetate (2×400 mL). The organic layers were washed with water and brine, dried (MgSO4) and concentrated in vacuum giving a dark oil that was crystallized from a 1/1 diethyl ether/petroleum ether mixture. Filtration of the solid obtained afforded 7.28 g of a white solid corresponding to the title compound (61% yield, 85% purity). This solid was used in the next step without further purifications.

Workup

  1. extractionextracted with ethyl acetate (2×400 mL)
  2. washThe organic layers were washed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuum
  5. customgiving a dark oil that
  6. customwas crystallized from a 1/1 diethyl ether/petroleum ether mixture
  7. filtrationFiltration of the solid
  8. customobtained

Sources & evidence

ORD record
ord-22b73261b6b840b091a3493a97701130
Source dataset
uspto-grants-2016_05
Patent number
US09340547B2

Reaction notes

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