Acetyl chloride → HCID 20468617, compound

HRID 1903353Notes

Reaction equation

HRID 1903353 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[OH:5][CH2:6][CH2:7][N:8]([CH3:32])[C:9](=[O:31])[C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[Cl:27])[CH:13]=[CH:12][C:11]=1[N+:28]([O-:30])=[O:29].C(N(CC)CC)C>C1COCC1>[C:1]([O:5][CH2:6][CH2:7][N:8]([CH3:32])[C:9](=[O:31])[C:10]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:24])[F:26])=[CH:19][C:18]=2[Cl:27])[CH:13]=[CH:12][C:11]=1[N+:28]([O-:30])=[O:29])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 20468635HCID 20468635, compound

Product 1

HCID 20468617HCID 20468617, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Acetyl chloride (2.7 g, 0.0344 mole) was added dropwise in 5 mins. to a solution of N-(2-hydroxyethyl)-N-methyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzamide (7.2 g, 0.0172 mole), triethylamine (25 ml) and THF (25 ml). The resulting mixture was heated up to and held at reflux for 2.5 hrs., cooled and concentrated. The residue was taken into 500 ml of ether, washed two times with water, dried over MgSO4 and concentrated to 8.6 g of crude product. The crude product was purified on a column of silica gel using ethyl acetate cyclohexane (1:3) as eluent to yield 3.5 g of pure N-[2-(acetoxy)ethyl]-N-methyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzamide as a gum; nmr (CDCl3) δ 2.04 (s, 3H), 2.92 (s)-3.15 (s) (3H), 3.40 (t)-3.79 (t) (2H); 4.12 (t)-4.40 (t) (2H), 6.80-8.42 (m, 6H); ir (CHCl3) 1750, 1655 Cm-1.

Workup

  1. temperatureThe resulting mixture was heated up to and
  2. temperatureat reflux for 2.5 hrs
  3. temperature, cooled
  4. concentrationconcentrated
  5. washwashed two times with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to 8.6 g of crude product
  8. customThe crude product was purified on a column of silica gel

Sources & evidence

ORD record
ord-a0bce7b280ae4998a825408ded189c92
Source dataset
uspto-grants-1984_03
Patent number
US04435588

Reaction notes

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