Chloroacetyl chloride → HCID 178468296, compound

HRID 1621155Notes

Reaction equation

HRID 1621155 reaction equation
Cl.[C:2](=[NH:12])([O:9][CH2:10][CH3:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:20][CH2:21][C:22](Cl)=[O:23]>ClC(Cl)C>[Cl:20][CH2:21][C:22](/[N:12]=[C:2](\[O:9][CH2:10][CH3:11])/[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:23]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 79249Benzenecarboximidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 178468296HCID 178468296, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of ethyl benzimidate hydrochloride (500 mg, 2.69 mmol) in dichloroethane (25 mL) was added under argon atmosphere triethylamine (872 mg, 1.2 mL, 8.62 mmol). The stirred reaction mixture was cooled to 0° C. and chloroacetyl chloride (608 mg, 431 μL, 5.39 mmol) was added. After 30 min the cooling bath was removed and stirring was continued at RT for 4 h. After filtration the organic phase was extracted with KHSO4 (10% aqueous solution), dried and evaporated to yield the product as light brown semi-solid (740 mg with 80% purity, 2.62 mmol, 97%) which was used without further purification for the next step.

Workup

  1. customThe stirred reaction mixture
  2. customAfter 30 min the cooling bath was removed
  3. filtrationAfter filtration the organic phase
  4. extractionwas extracted with KHSO4 (10% aqueous solution)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-67fdfbf6c13b43438c6ff24cc502aa2c
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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