Acetyl chloride → HCID 67966825, compound

HRID 527659Notes

Reaction equation

HRID 527659 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]([OH:13])([CH3:12])[CH3:11].C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22].[NH4+].[Cl-]>C(Cl)Cl>[OH:13][C:10]([C:3]1[C:4]([O:8][CH3:9])=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:21](=[O:23])[CH3:22])([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 67958514HCID 67958514, compound2×

Product 1

HCID 67966825HCID 67966825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(2-Amino-6-methoxyphenyl)propan-2-ol (Intermediate 199, 500 mg, 2.76 mmol) was dissolved in DCM (10 mL) and triethylamine (0.770 ml, 5.52 mmol) was added. The solution was cooled to 0° C. and treated with acetyl chloride (0.2 ml, 2.76 mmol) in a drop wise fashion. At the end of the addition, complete conversion was reached. The mixture was treated with an aqueous saturated solution of NH4Cl, two phases were separated and the organic layer was washed with an aqueous saturated solution of NaHCO3 and brine, then dried over Na2SO4 and evaporated to dryness. The crude was purified by re-slurry in tert-butyl methyl ether isolating 490 mg of the title compound as white solid.

Workup

  1. additionAt the end of the addition, complete conversion
  2. customwere separated
  3. washthe organic layer was washed with an aqueous saturated solution of NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude was purified by re-slurry in tert-butyl methyl ether isolating 490 mg of the title compound as white solid

Sources & evidence

ORD record
ord-5301aa62c5f344e187fa6bfdc206ada3
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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