Chloroacetyl chloride → HCID 178468297, compound

HRID 1621163Notes

Reaction equation

HRID 1621163 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6](=[NH:10])[O:7][CH2:8][CH3:9].C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>ClCCl>[Cl:21][CH2:22][C:23](/[N:10]=[C:6](\[O:7][CH2:8][CH3:9])/[C:5]1[CH:11]=[CH:12][CH:13]=[C:3]([F:2])[CH:4]=1)=[O:24]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 12282165Benzenecarboximidic acid, 3-fluoro-, ethyl ester, hydrochloride

Product 1

HCID 178468297HCID 178468297, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

To a suspension of ethyl 3-fluorobenzimidate hydrochloride (400 mg, 1.96 mmol) in dichloromethane (15 mL) was added triethylamine (497 mg, 684 μL, 4.91 mmol) at RT. The reaction mixture was cooled to 0-5° C. and 2-chloroacetyl chloride (333 mg, 234 μL, 2.95 mmol) was added dropwise over a period of 5 min. After 20 min the ice bath was removed and the mixture was stirred at RT for 2 h. The reaction mixture was poured into KHSO4 (10% aqueous solution, 25 mL) and extracted with dichloromethane (3×50 mL). The combined organic layer was dried over MgSO4 and concentrated in vacuo to give the product as light brown oil (537 mg, 1.98 mmol, 101%) which was used without further purification for the next step.

Workup

  1. customAfter 20 min the ice bath was removed
  2. additionThe reaction mixture was poured into KHSO4 (10% aqueous solution, 25 mL)
  3. extractionextracted with dichloromethane (3×50 mL)
  4. dry with materialThe combined organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4f3a642ca4e4c9faec9dc55c7f5208c
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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