Hydrochloric Acid → methyl alpha-(4-(N-methylcarbamyl)aminosulfonyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetate

HRID 1378871Notes

Reaction equation

HRID 1378871 reaction equation
[NH2:1][S:2]([C:5]1[CH:25]=[CH:24][C:8]([O:9][CH:10]([C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][O:23][C:17]=3[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[C:7]([CH2:26][CH2:27][CH3:28])[CH:6]=1)(=[O:4])=[O:3].[CH3:29][N:30]=[C:31]=[O:32].C(N(CC)CC)C.Cl>CN(C)C=O.CO.C(Cl)Cl>[CH3:29][NH:30][C:31]([NH:1][S:2]([C:5]1[CH:25]=[CH:24][C:8]([O:9][CH:10]([C:15]2[CH:20]=[CH:19][C:18]3[O:21][CH2:22][O:23][C:17]=3[CH:16]=2)[C:11]([O:13][CH3:14])=[O:12])=[C:7]([CH2:26][CH2:27][CH3:28])[CH:6]=1)(=[O:3])=[O:4])=[O:32]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12228Methyl Isocyanate2×HCID 19080400Methyl alpha-(2-n-propyl-4-aminosulfonyl-phenoxy)-3,4-methylenedioxyphenylacetate2×

Product 1

HCID 53963621methyl alpha-(4-(N-methylcarbamyl)aminosulfonyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226129Dichloromethane methanolSolvent2×

Procedure

To a stirred solution of 500 mg (1.23 mmol) of methyl α-(4-aminosulfonyl-2-n-propylphenoxy)-3,4-methylenedioxyphenylacetate (the product of Example 100, Step C) in dry dimethylformamide (2 mL) was added 80 μL (1.35 mmol) of methyl isocyanate followed by 6 mg (0.06 mmol) of cuprous chloride. The reaction mixture was stirred overnight, after which TLC analysis (5% methanol/methylene chloride) indicated the reaction had not proceeded to completion. Subsequently, an additional 80 μL (1.35 mmol) of methyl isocyanate, 6 mg (0.06 mmol) of cuprous chloride as well as 342 μL (2.46 mmol) of triethylamine was added and the reaction mixture was again stirred overnight. TLC analysis (5% methanol/methylene chloride) indicated the reaction had proceeded to completion. The reaction mixture was poured into 1N HCl and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo and dried to afford 570 mg (100%) of the title compound as an amorphous solid.

Workup

  1. waitthe reaction mixture was again stirred overnight
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customdried

Sources & evidence

ORD record
ord-41b1c17ea1b04ca4aa1e85338a3a1b1d
Source dataset
uspto-grants-1997_09
Patent number
US05668176

Reaction notes

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