Triethylamine → HCID 68670050, compound

HRID 2071058Notes

Reaction equation

HRID 2071058 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]([CH:13]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].CCN(CC)CC.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([NH:1][CH2:2][C:3]1[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[C:5]([CH:4]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68671552HCID 68671552, compound

Product 1

HCID 68670050HCID 68670050, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of crude diethyl 5-(aminomethyl)isophthalate in 30 mL of CH2Cl2 at 0° C. was added 1.2 mL of Et3N and 0.7 mL of MsCl. The ice bath was removed, and after 2 h at r.t. the solution was concentrated, and EtOAc and H2O were added. The organic layer was washed with brine, the aqueous layer was extracted with EtOAc, the combined extracts were dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1% MeOH/CHCl3) provided 901 mg of diethyl 5-(methylsulfonamidomethyl)isophthalate as a pale yellow solid in 35% yield.

Workup

  1. customThe ice bath was removed
  2. concentrationafter 2 h at r.t. the solution was concentrated
  3. additionEtOAc and H2O were added
  4. washThe organic layer was washed with brine
  5. extractionthe aqueous layer was extracted with EtOAc
  6. dry with materialthe combined extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by flash silica gel chromatography (1% MeOH/CHCl3)

Sources & evidence

ORD record
ord-6d479df1c0144b438a5f1fc60fc7ae2c
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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