Ammonia → HCID 89875789, compound

HRID 1487038Notes

Reaction equation

HRID 1487038 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:22]=[CH:21][C:16]([C:17](OC)=[O:18])=[CH:15][CH:14]=1)(=[O:12])=[O:11].N.O1CCOCC1.[Li+].C[Si]([N-:39][Si](C)(C)C)(C)C>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[S:10]([C:13]1[CH:22]=[CH:21][C:16]([C:17]([NH2:39])=[O:18])=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 312751,4-DioxaneHCID 2733832Lithium HexamethyldisilazideHCID 86731611HCID 86731611, compound

Product 1

HCID 89875789HCID 89875789, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)benzoate (280 mg, 0.746 mmol) was dissolved in tetrahydrofuran (THF) (5 mL) and to this solution was added ammonia in dioxane (0.5 M) (4.47 mL, 2.237 mmol), followed by LiHMDS in THF (1 M, 0.895 mL, 0.895 mmol). The reaction was left to stir overnight at room temperature, under nitrogen. The reaction was quenched with water (1 mL) then combined with a previous identical trial reaction on a smaller (0.075 mmol) scale, for workup. The crude was concentrated in vacuo, then the product was extracted to the organic phase of an aqueous work up between ethyl acetate (15 mL) and brine (10 mL). The organic phase was passed through a hydrophobic frit and concentrated in vacuo to give the crude product, 263 mg. No further purification was undertaken. LCMS [LCMS1] Rt 1.14 min, m/z (ES+) 361 (M+H).

Workup

  1. waitThe reaction was left
  2. customThe reaction was quenched with water (1 mL)
  3. customthen combined with a previous identical trial reaction on a smaller (0.075 mmol) scale, for workup
  4. concentrationThe crude was concentrated in vacuo
  5. extractionthe product was extracted to the organic phase of an aqueous work up between ethyl acetate (15 mL) and brine (10 mL)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96d0a13115114951926c81cd77972b78
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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