Triethylamine → HCID 68291399, compound

HRID 2174553Notes

Reaction equation

HRID 2174553 reaction equation
[C:1]1([S:7]([CH2:10][C:11]([OH:13])=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[NH2:20][C:21]1[CH:30]=[C:29]([Cl:31])[C:28]([I:32])=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].C(N(CC)CC)C>ClCCl.CN(C=O)C>[Cl:31][C:29]1[C:28]([I:32])=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([NH:20][C:11](=[O:13])[CH2:10][S:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)(=[O:8])=[O:9])[CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 59543(phenylsulfonyl)acetic acidHCID 65578Oxalyl chlorideHCID 10852539Methyl 2-amino-4-chloro-5-iodobenzoate2×

Product 1

HCID 68291399HCID 68291399, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(phenylsulfonyl) acetic acid (Lancaster Synthesis Ltd., 0.771 mg, 3.85 mmol) in dichloromethane (50 mL) was added oxalyl chloride (4.17 mL, 4.17 mmol) and few drops of DMF. The reaction mixture was stirred 2 hours at room temperature. To a solution of methyl 2-amino-4-chloro-5-iodobenzoate (Intermediate 2) (1 g, 3.21 mmol) and triethylamine (1.074 mL, 7.70 mmol) in dichloromethane (50 mL) at RT was added dropwise the acid chloride prepared above. The reaction mixture was stirred at room temperature overnight then quenched with aqueous solution of NaHCO3. The organic layer was and washed with saturated NaHCO3, water and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give the title compound methyl 4-chloro-5-iodo-2-(2-(phenylsulfonyl)acetamido)benzoate (1.1 g, 2.228 mmol, 69.4% yield) as pale yellow powder. LCMS: (M+H)+=494; Rt=3.58 min.

Workup

  1. customprepared above
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. customthen quenched with aqueous solution of NaHCO3
  4. washwashed with saturated NaHCO3, water and brine
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-338cb3d0963e4523bdc247c3fa9d0e51
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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