Hydrochloric Acid → 3-[[(1,1-dimethylethyl)amino]sulfonyl]N,N,1-trimethyl-1H-pyrrole-2-carboxamide

HRID 2259188

反応式

HRID 2259188 の反応式
[CH3:1][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[CH3:20][N:21]([CH3:25])[C:22](Cl)=[O:23].[Cl-].[NH4+].Cl>C1COCC1>[CH3:4][C:2]([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:22]([N:21]([CH3:25])[CH3:20])=[O:23])(=[O:8])=[O:7])([CH3:1])[CH3:3]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6598Dimethylcarbamoyl ChlorideHCID 25517Ammonium ChlorideHCID 19693811N-(1,1-Dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamideHCID 178418339Butyllithium

生成物 1

HCID 196938293-[[(1,1-dimethylethyl)amino]sulfonyl]N,N,1-trimethyl-1H-pyrrole-2-carboxamide収率 50.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -60° C., 25 mL (61.5 mmol) 2.46M n-butyllithium in hexanes. The reaction mixture was stirred at -78° C. for ca. 30 minutes. To the reaction mixture was added dropwise a solution of 3.1 mL (33 mmol) of N,N-dimethylcarbamyl chloride in 10 mL of THF at such a rate as to maintain the temperature below -65° C. The reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to ca. 5° C. and 60 mL of 50% ammonium chloride solution was added. The reaction mixture was stirred for ca. 15 minutes. The pH was adjusted to ca. 3 with 1N HCl (ca. 30 mL), and the aqueous phase was separated from the THF phase and extracted with ethyl acetate. The combined THF and ethyl acetate extracts were washed with brine, dried (MgSO4) and concentrated in vacuo to an oil. The oil was chromatographed on silica with (20% ethyl acetate/80% n-butyl chloride) affording 4.33 g of the title compound as a pale yellow solid. 1H NMR(CDCl3, 200 MHz.) δ: 6.61(d,1H), 6.46(d,1H), 4.62(bs,1H), 3.59(s,3H), 3.1(s,3H), 2.95(s,3H), 1.24(s,9H).

後処理

  1. additionwas added dropwise
  2. temperatureto maintain the temperature below -65° C
  3. temperatureto warm to room temperature
  4. stirringstir for ca. 1.5 hours
  5. temperatureThe reaction mixture was cooled to ca. 5° C.
  6. stirringThe reaction mixture was stirred for ca. 15 minutes
  7. customthe aqueous phase was separated from the THF phase
  8. extractionextracted with ethyl acetate
  9. washThe combined THF and ethyl acetate extracts were washed with brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo to an oil
  12. customThe oil was chromatographed on silica with (20% ethyl acetate/80% n-butyl chloride)

出典と根拠

ORDレコード
ord-ffff5bf61fa54d068a9cc8181f6acc32
出典データセット
uspto-grants-1995_12
特許番号
US05472933

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