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Water → 2-Amino-2-[2-(trifluoromethyl)phenyl]ethyl carbamate hydrochloride

HRID 2402775
ノート
印刷プレビュー

反応式

HRID 2402775 の反応式
[OH:1][CH2:2][CH:3]([NH:14]C(=O)OC(C)(C)C)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([F:13])([F:12])[F:11].[Cl:22]S([N:26]=[C:27]=[O:28])(=O)=O.O.C(=O)([O-])O.[Na+]>C(#N)C>[ClH:22].[C:27](=[O:28])([O:1][CH2:2][CH:3]([NH2:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]([F:11])([F:12])[F:13])[NH2:26]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 59536783tert-Butyl {2-hydroxy-1-[2-(trifluoromethyl)phenyl]ethyl}carbamate

生成物 1

HCID 686461242-Amino-2-[2-(trifluoromethyl)phenyl]ethyl carbamate hydrochloride

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

反応条件

温度
60 °C

実験手順

A solution of 570 mg (1.87 mmol) of the compound from Example 62A in 100 ml of acetonitrile was cooled to −15° C. and admixed with 325 μl (3.73 mmol) of chlorosulphonyl isocyanate. After 10 min, 50 ml of water were added and the mixture was heated at 60° C. for 4 h. After cooling to RT, the solution was rendered alkaline (pH 9-10) by addition of saturated aqueous sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvents on a rotary evaporator. For complete deprotection of the amino group, the residue was admixed with 15 ml of a 4M solution of hydrogen chloride in dioxane, and the mixture was stirred at RT for 5 min and the volatile components were removed on a rotary evaporator. The residue corresponded to the title compound (630 mg, quant.).

後処理

  1. temperatureAfter cooling to RT
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. customfreed from the solvents on a rotary evaporator
  5. customthe volatile components were removed on a rotary evaporator

出典と根拠

ORDレコード
ord-68011f39fb0d41bfbd8c63cbddce3552
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08796324B2

反応ノート

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