Chlorosulfamic acid → 2-Methylphenethyl sulfamate

HRID 414605

反応式

HRID 414605 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[CH2:4][CH2:5][OH:6].[H-].[Na+].[S:13](Cl)(=[O:16])(=[O:15])[NH2:14]>CN(C=O)C>[S:13](=[O:16])(=[O:15])([O:6][CH2:5][CH2:4][C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[CH3:1])[NH2:14]

参加物

5

反応物 3

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 882672-Methylphenethyl alcohol

生成物 1

HCID 144420722-Methylphenethyl sulfamate収率 43%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A mixture of 2.65 g (0.019 mole) of 2-methylphenethyl alcohol in 10 ml DMF was added dropwise to a suspension of sodium hydride (1.1 g, 60% in oil; 0.08 mole) in 35 ml DMF at 0°-5° C. The suspension was stirred for 20 min under argon after which sulfamoyl chloride (2.86 g, 0.02 mole) was added portion wise at 0°-5° C. After stirring for 20 min the resultant suspension was poured into ice and extracted twice with Et2O. The combined organic phases were washed with saturated brine, dried over potassium carbonate and concentrated in vacuo to a syrup which was purified by preparative HPLC with hexane/EtOAc (1:1, v/v) as the eluant to give 1.76 g (43%) of the title compound as a solid, mp 50°-52° C.

後処理

  1. additionwas added portion wise at 0°-5° C
  2. additionwas poured into ice
  3. extractionextracted twice with Et2O
  4. washThe combined organic phases were washed with saturated brine
  5. dry with materialdried over potassium carbonate
  6. concentrationconcentrated in vacuo to a syrup which
  7. customwas purified by preparative HPLC with hexane/EtOAc (1:1

出典と根拠

ORDレコード
ord-2f5d1101dde04deb99bdb5cae35fc23d
出典データセット
uspto-grants-1988_12
特許番号
US04792569

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