Water → N2-(3-acetoxymethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamide

HRID 2229921Notes

Reaction equation

HRID 2229921 reaction equation
[CH3:1][C:2]1[C:6]([CH3:7])=[C:5]([N:8]([CH2:20][O:21][CH3:22])[S:9]([C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:17](Cl)=[O:18])(=[O:11])=[O:10])[O:4][N:3]=1.[C:23]([O:26][CH2:27][C:28]1[C:29]([CH3:37])=[C:30]([C:32]([CH3:36])=[CH:33][C:34]=1[CH3:35])[NH2:31])(=[O:25])[CH3:24].C(N(CC)CC)C.O>ClCCl.CN(C)C1C=CN=CC=1>[C:23]([O:26][CH2:27][C:28]1[C:29]([CH3:37])=[C:30]([NH:31][C:17]([C:13]2[S:14][CH:15]=[CH:16][C:12]=2[S:9]([N:8]([C:5]2[O:4][N:3]=[C:2]([CH3:1])[C:6]=2[CH3:7])[CH2:20][O:21][CH3:22])(=[O:11])=[O:10])=[O:18])[C:32]([CH3:36])=[CH:33][C:34]=1[CH3:35])(=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 105228213-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarbonyl chlorideHCID 106559423-Acetoxymethyl-2,4,6-trimethylaniline

Product 1

HCID 54548392N2-(3-acetoxymethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamideYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarbonyl chloride (1.1 g, 2.97 mmol) in dichloromethane (9 mL) was added 3-acetoxymethyl-2,4,6-trimethylaniline (0.6 g, 2.97 mmol) at 0° C. Triethylamine (0.46 mL, 3.26 mmol) and 4-dimethylaminopyridine (36 mg, 0.30 mmol) were added. The mixture was stirred at room temperature overnight, then mixed with water (10 mL). The organic material was separated, and the aqueous layer was extracted with dichloromethane (2×10 mL). The extracts were combined and washed with water (20 mL) and saturated sodium chloride (20 mL), dried (MgSO4), then concentrated. The residue was purified by flash chromatography (SiO2, hexane:ethyl acetate/2:1) to give N2-(3-acetoxymethyl-2,4,6-trimethylphenyl)-3-[N-(3,4-dimethylisoxazol-5-yl)-N-methoxymethylaminosulfonyl]-2-thiophenecarboxamide (0.79 g, 50%) as a yellow oil.

Workup

  1. customThe organic material was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (2×10 mL)
  3. washwashed with water (20 mL) and saturated sodium chloride (20 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (SiO2, hexane:ethyl acetate/2:1)

Sources & evidence

ORD record
ord-ae75617d29a440b0a7bc9243825a5075
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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