Chloroacetyl chloride → 2-Chloro-N-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamide

HRID 2298434Notes

Reaction equation

HRID 2298434 reaction equation
[CH3:1][C:2]1[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:3]=1[O:4][C:5]1[C:10]([NH2:11])=[C:9]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[CH:8]=[C:7]([CH3:18])[N:6]=1.C(N(CC)CC)C.[Cl:32][CH2:33][C:34](Cl)=[O:35]>C1COCC1>[Cl:32][CH2:33][C:34]([NH:11][C:10]1[C:5]([O:4][C:3]2[C:19]([CH3:24])=[CH:20][C:21]([CH3:23])=[CH:22][C:2]=2[CH3:1])=[N:6][C:7]([CH3:18])=[CH:8][C:9]=1[NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])=[O:35]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 219121512-(2,4,6-trimethylphenoxy)-N4-(1-ethylpropyl)-6-methyl-pyridine-3,4-diamine

Product 1

HCID 120183492-Chloro-N-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamideYield 101%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(2,4,6-trimethyl-phenoxy)-N4-(1-ethyl-propyl)-6-methyl-pyridine-3,4-diamine (250 mg, 0.76 mmol) and triethylamine (0.11 ml, 0.76 mmol) in 5 ml of dry THF was treated with chloroacetyl chloride (0.06 ml, 0.76 mmol) at 0° C. The resulting mixture was stirred at room temperature for 1 hour. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried and concentrated to give 310 mg of green crystals that was purified through silica gel column chromatography using 10% ethyl acetate in hexane as eluent to give 280 mg (90%) of the title compound as tan crystals, mp 152-154° C. 1H NMR (CDCl3) δ 8.07(s,1H), 6.88(s,2H), 6.16(s,1H), 4.75(brs,1H), 4.25(s,2H), 3.33(m,1H), 2.30(s,3H), 2.18(s,3H), 2.08(s,6H), 1,4-1.8(m,4H), 0.97(t,6H) ppm.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ceeb13186d8349dd84c313b4822abc05
Source dataset
uspto-grants-2002_12
Patent number
US06492520B1

Reaction notes

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