Chloroacetyl chloride → HCID 16495703, compound

HRID 1257581Notes

Reaction equation

HRID 1257581 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].C(N(CC)CC)C.[Cl:20][CH2:21][C:22](Cl)=[O:23]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:22](=[O:23])[CH2:21][Cl:20]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 5972502,4-Dimethoxybenzylamine

Product 1

HCID 16495703HCID 16495703, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-dimethoxybenzylamine (1.50 mL, 10.0 mmol) and triethylamine (2.00 mL, 14.3 mmol) in tetrahydrofuran (20 mL) at 0° C. was added chloroacetyl chloride (0.80 mL, 10 mmol). The reaction was then stirred at 0° C. for three hours. The crude reaction mixture was partitioned between ethyl acetate and water, and the organic layer dried over brine and magnesium sulfate, filtered, and evaporated in vacuo to yield 2.2074 g (91%) of N-(2,4-Dimethoxy-benzyl)-2-chloro-acetamide which was carried forward without purification. LCMS (Method E, ESI): RT=1.43 min, m+H=244.2

Workup

  1. customThe crude reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. dry with materialthe organic layer dried over brine and magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-311de4145aa8459984ba50883da33acb
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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