Triethylamine → Benzothiazole, 5-methoxy-2-(beta-(1-pyrrolidinyl)-p-phenetidino)-

HRID 1076834노트

반응식

HRID 1076834 반응식
C(N(CC)CC)C.Cl.[NH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[SH:18].[N:19]1([CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]=[C:34]=S)=[CH:29][CH:28]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:17][O:16][C:14]1[CH:13]=[CH:12][C:11]2[S:18][C:34]([NH:33][C:30]3[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[CH:28][CH:29]=3)=[N:9][C:10]=2[CH:15]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 118461221-(2-(4-Isothiocyanatophenoxy)ethyl)pyrrolidineHCID 121992962-Amino-4-methoxybenzene-1-thiol hydrochloride

생성물 1

HCID 38054Benzothiazole, 5-methoxy-2-(beta-(1-pyrrolidinyl)-p-phenetidino)-

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

Triethylamine (0.7 ml.) is added to a suspension of 2-amino-4-methoxybenzenethiol hydrochloride (0.96 g.) in toluene (20 ml.) under nitrogen. 4-(2-Pyrrolidin-1-ylethoxy)phenyl isothiocyanate (1.24 g.) is added and the mixture stirred and heated under reflux for 16 hours. Ethyl acetate and 10% sodium hydroxide are added and the organic layer separated, washed with water and dried. The organic layer is passed through a column of silica gel (2 × 20 cm.) and the filtrate rejected. The column is eluted with methanol, which, on concentration gives 5-methoxy-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]benzothiazole, m.p. 167° - 168°C.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 16 hours
  3. customthe organic layer separated
  4. washwashed with water
  5. customdried
  6. washThe column is eluted with methanol, which, on concentration

출처 및 근거

ORD 기록
ord-8212335d39954d859208caa13f472fa5
출처 데이터셋
uspto-grants-1976_05
특허 번호
US03957999

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