Water → HCID 19974714, compound

HRID 1451509Notes

Reaction equation

HRID 1451509 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH:11]([CH3:13])[CH3:12].C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24].O>ClCCl>[Cl:21][CH2:22][C:23]([N:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Cl:1])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 19974708HCID 19974708, compound

Product 1

HCID 19974714HCID 19974714, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the above amine (15.0 g, 74 mmol) and triethylamine (12.0 g, 119 mmol) in dichloromethane (200 ml) was cooled to -10° C. and chloroacetyl chloride (11.3 g, 113 mmol) was carefully added while the temperature was kept below 10° C. The mixture was then stirred at ambient temperature for 1 h. The reaction mixture was poured into water (200 ml) and extracted with dichloromethane (2×100 ml). The organic phase was washed with 4N hydrochloric acid (2×50 ml), water (100 ml) and saturated aqueous sodium hydrogencarbonate (50 ml) and dried (MgSO4). The solvent was evaporated in vacuo to give 13.6 g of 2-chloro-N-(2-chloro-4-fluorophenyl)-N-(2-methyl-1-propyl)acetamide.

Workup

  1. customwas kept below 10° C
  2. extractionextracted with dichloromethane (2×100 ml)
  3. washThe organic phase was washed with 4N hydrochloric acid (2×50 ml), water (100 ml) and saturated aqueous sodium hydrogencarbonate (50 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-74b61b63eb994fb1b120d72d11ffe0a2
Source dataset
uspto-grants-1997_02
Patent number
US05604242

Reaction notes

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