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

HRID 1861998Notes

Reaction equation

HRID 1861998 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]>CN(C=O)C>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([O:16][S:25]([CH3:24])(=[O:27])=[O:26])[CH:12]=[CH:11]2)=[O:4]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 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 crude alcohol from Step A (50.3 mmol) in 150 mL of DMF at 0° C. was added triethylamine (15.0 mL, 108 mmol), followed by dropwise addition of methanesulfonyl chloride (6.0 mL, 77.5 mmol). After 16 hours, additional portions of triethylamine (7.0 mL, 50 mmol) and methanesulfonyl chloride (3.0 mL, 39 mmol) were added. After 4 hours, the solution was concentrated in vacuo and partitioned between EtOAc and saturated NH4Cl solution. The organic layer was extracted with saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide a dark purple solid.

Workup

  1. waitAfter 4 hours
  2. concentrationthe solution was concentrated in vacuo
  3. custompartitioned between EtOAc and saturated NH4Cl solution
  4. extractionThe organic layer was extracted with saturated NaHCO3 solution and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a dark purple solid

Sources & evidence

ORD record
ord-68080fe4a3354e46b6c7e7f9849ca517
Source dataset
uspto-grants-2003_03
Patent number
US06534506B2

Reaction notes

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