Sodium hydride → 3-Acetyl-2-[2-(3-dimethylaminopropoxy)phenyl]benzothiazoline

HRID 1583662

반응식

HRID 1583662 반응식
[H-].[Na+].[C:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21])(=[O:5])[CH3:4].[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26]Cl>CN(C=O)C>[C:3]([N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][CH:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:22])(=[O:5])[CH3:4]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 133359603-Acetyl-2-(2-hydroxyphenyl)benzothiazoline

생성물 1

HCID 133357593-Acetyl-2-[2-(3-dimethylaminopropoxy)phenyl]benzothiazoline수율 56%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

To the suspension of 0.26 g of the sodium hydride in anhydrous DMF, the solution of 1.36 g of 3-acetyl-2-(2-hydroxyphenyl)benzothiazoline in 5 ml of anhydrous DMF is added dropwise under nitrogen atmosphere at room temperature. After the addition, the reaction mixture is stirred for 20 minutes at room temperature. To the reaction mixture, the solution of 0.61 g of 3-dimethylaminopropyl chloride in 10 ml of anhydrous DMF is added. The reaction mixture is stirred for 2 hours at 80° C., and washed with n-hexane after cooling and poured into ice-water. The separated oil is extracted with ethyl acetate. The organic layer is washed with N--NaOH solution, water and saturated sodium chloride solution in the order named and dried over anhydrous magnesium sulfate. Ethy acetate is removed off in vacuo to give 1.0 g (56%) of the titled compound.

후처리

  1. additionAfter the addition
  2. stirringThe reaction mixture is stirred for 2 hours at 80° C.
  3. washwashed with n-hexane
  4. temperatureafter cooling
  5. additionpoured into ice-water
  6. extractionThe separated oil is extracted with ethyl acetate
  7. washThe organic layer is washed with N
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customEthy acetate is removed off in vacuo

출처 및 근거

ORD 기록
ord-843d9fe9fbcc4a24a3031fab2a6bbfba
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04552969

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