Ethyl thiocyanate → (2-Amino-benzothiazol-6-yl)-acetic acid ethyl ester

HRID 1790387

반응식

HRID 1790387 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C([S:16][C:17]#[N:18])C.BrBr.[OH-].[Na+]>C(O)(=O)C>[NH2:18][C:17]1[S:16][C:7]2[CH:6]=[C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[CH:3][C:2]=2[N:1]=1

참가 물질

6

반응물 4

HCID 10968Ethyl thiocyanateHCID 14798Sodium HydroxideHCID 24408BromineHCID 225219p-Aminophenylacetic acid ethyl ester

생성물 1

HCID 821202(2-Amino-benzothiazol-6-yl)-acetic acid ethyl ester수율 93.7%

시약·촉매·용매 1

HCID 176Acetic Acid용매

반응 조건

온도
10 °C

실험 절차

Ethyl 4-aminophenylacetate (18 g) was dissolved in acetic acid (120 ml) and ethyl thiocyanate (29.3 g) was added thereto. Under ice cooling, bromine (6.2 ml) was added dropwise thereinto over 45 minutes while maintaining the reaction temperature at about 10° C. After the completion of the addition, the resultant mixture was stirred at room temperature for 1.5 hr and then at 80° C. for about 2 hr until the reaction was completed. Then the reaction solution was poured into ice water, basified with an 8 N aqueous solution of sodium hydroxide, extracted with chloroform, washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give the title compound (22.23 g) as orange crystals (yield: 93.66%).

후처리

  1. additionAfter the completion of the addition
  2. extractionextracted with chloroform
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-95b25d98d1334363b00baa78d11a4e52
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071201B2

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