Triethylamine → 1-(Chloroacetamido)-7-[(methanesulfonyl)oxy]naphthalene

HRID 412170Notes

Reaction equation

HRID 412170 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([OH:16])[CH:14]=2)[CH:9]=[CH:8][CH:7]=1)=[O:4].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].CCOC(C)=O>CN(C)C=O>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH:14]=2)[CH:9]=[CH:8][CH:7]=1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 186212152-chloro-N-(7-hydroxynaphthalen-1-yl)acetamide

Product 1

HCID 155493251-(Chloroacetamido)-7-[(methanesulfonyl)oxy]naphthalene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product from Step C (14.0 g, 59.4 mmol) in 180 mL of dimethylformamide at 0° C. was added triethylamine (26.3 mL, 190 mmol), followed by methanesulfonyl chloride (10.5 mL, 137 mmol). The reaction was stirred overnight, allowing it to warm to room temperature. The solution was poured into EtOAc, washed with saturated NH4Cl solution, saturated aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was used without further purification.

Workup

  1. washwashed with saturated NH4Cl solution, saturated aq. NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting product was used without further purification

Sources & evidence

ORD record
ord-5596d1390e8f41f8903b0c3d04768844
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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