Water → 2-Amino-2-(2,3-dichlorophenyl)ethyl carbamate

HRID 2402830ノート

反応式

HRID 2402830 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]([NH:12]C(=O)OC(C)(C)C)[CH2:10][OH:11].ClS([N:24]=[C:25]=[O:26])(=O)=O.O.C(=O)([O-])O.[Na+]>C(#N)C>[C:25](=[O:26])([O:11][CH2:10][CH:9]([NH2:12])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([Cl:8])[C:2]=1[Cl:1])[NH2:24]

参加物

6

反応物 4

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 59536916tert-butyl N-[1-(2,3-dichlorophenyl)-2-hydroxyethyl]carbamate

生成物 1

HCID 595368632-Amino-2-(2,3-dichlorophenyl)ethyl carbamate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

Of the compound from Example 182A, 290 mg (about 0.95 mmol) were introduced in 5 ml of acetonitrile under argon. At −15° C., 115 μl (1.33 mmol) of chlorosulphonyl isocyanate were added dropwise. After 30 min, the reaction solution was admixed with 20 ml of water and heated at 60° C. overnight. The reaction mixture was cooled and introduced into saturated aqueous sodium hydrogen carbonate solution. It was extracted with twice 20 ml of ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and freed from the solvent on a rotary evaporator. Drying in an HV gave 176 mg (66% of theory) of the title compound in 89% purity.

後処理

  1. temperatureThe reaction mixture was cooled
  2. extractionIt was extracted with twice 20 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. customfreed from the solvent on a rotary evaporator
  6. customDrying in an HV

出典と根拠

ORDレコード
ord-2c06a0bc31474d8b81dcd78e360655a0
出典データセット
uspto-grants-2014_08
特許番号
US08796324B2

反応ノート

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