Riluzole → 3-(2-Acetamidoethyl)-2-imino-6-trifluoromethoxybenzothiazoline

HRID 1111369

반응식

HRID 1111369 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl[CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21].[I-].[Na+]>C(C(C)=O)C>[C:20]([NH:19][CH2:18][CH2:17][N:6]1[C:5]2[CH:7]=[CH:8][C:9]([O:11][C:12]([F:15])([F:13])[F:14])=[CH:10][C:4]=2[S:3][C:2]1=[NH:1])(=[O:22])[CH3:21]

참가 물질

5

반응물 3

HCID 5070RiluzoleHCID 5238Sodium IodideHCID 81815N-(2-Chloroethyl)acetamide

생성물 1

HCID 30764113-(2-Acetamidoethyl)-2-imino-6-trifluoromethoxybenzothiazoline수율 21.1%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

반응 조건

온도
20 °C

실험 절차

2-Amino-6-trifluoromethoxybenzothiazole (9.4 g), N-(2-chloroethyl)acetamide (9.7 g) and sodium iodide (13.5 g) in methyl ethyl ketone (30 cc) are heated for 40 hours to boiling. After cooling to a temperature in the region of 20° C., the reaction medium is added to distilled water (200 cc), treated with 1N sodium hydroxide (40 cc) and then extracted with ethyl acetate (200 cc). After drying over magnesium sulphate and then concentration to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa), the residue is purified by chromatography on a silica column with a mixture of ethyl acetate and methanol (90:10 by volume) as eluent. 3-(2-Acetamidoethyl)-2-imino-6-trifluoromethoxybenzothiazoline (2.7 g) is obtained, which product is converted to a hydrochloride subliming at about 180° C.

후처리

  1. additionthe reaction medium is added
  2. distillationto distilled water (200 cc)
  3. additiontreated with 1N sodium hydroxide (40 cc)
  4. extractionextracted with ethyl acetate (200 cc)
  5. dry with materialAfter drying over magnesium sulphate
  6. concentrationconcentration to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  7. customthe residue is purified by chromatography on a silica column with a mixture of ethyl acetate and methanol (90:10 by volume) as eluent

출처 및 근거

ORD 기록
ord-5adc69eb76704e68ba0a32ca3e20db64
출처 데이터셋
uspto-grants-1990_12
특허 번호
US04980356

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