Chloroacetyl chloride → HCID 18519345, compound

HRID 1369299Notes

Reaction equation

HRID 1369299 reaction equation
[CH3:1][C:2]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:6]=[C:5]([CH3:18])[C:3]=1[NH2:4].CCN(C(C)C)C(C)C.[Cl:28][CH2:29][C:30](Cl)=[O:31]>ClCCl>[Cl:28][CH2:29][C:30]([NH:4][C:3]1[C:2]([CH3:1])=[CH:8][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:6][C:5]=1[CH3:18])=[O:31]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 18519348HCID 18519348, compound

Product 1

HCID 18519345HCID 18519345, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, 2,6-dimethyl-4-(octyloxy)-aniline (7.2 mmols) was dissolved in 50 mL dichloromethane. To this was added DIPEA (9.4 mmols). The reaction mixture was cooled in an ice bath, and chloroacetyl chloride (7.95 mmoles) dissolved in 50 mL dichloromethane was added by dropping funnel. After the addition was complete, the reaction was stirred at room until reaction was complete by TLC (approximately 0.5 hours). The reaction mixture was concentrated, and partitioned between ethyl acetate and water. The organic layer was washed with saturated NaHCO3 (×2), brine, dried over MgSO4, and filtered (rinsing with ethyl acetate). The filtrate was concentrated to yield 2-chloro-N-(2,6-dimethyl-4-octyloxyphenyl)-acetamide as a white solid (1.21 grams; 51%). The product was characterized by NMR (DMSO).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. additionwas added
  3. additionAfter the addition
  4. customwas complete by TLC (approximately 0.5 hours)
  5. concentrationThe reaction mixture was concentrated
  6. custompartitioned between ethyl acetate and water
  7. washThe organic layer was washed with saturated NaHCO3 (×2), brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. wash(rinsing with ethyl acetate)
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c794e845cd4e45b58d25be685ee5276a
Source dataset
uspto-grants-2003_06
Patent number
US06576791B1

Reaction notes

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