Methane → Metoclopramide sulfide

HRID 1382960

반응식

HRID 1382960 반응식
Cl.[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:8])=[C:5]([OH:20])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:29][S:30][CH2:31][CH2:32]Cl.C>CN(C=O)C.C(#N)C>[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])=[O:8])=[C:5]([O:20][CH2:32][CH2:31][S:30][CH3:29])[CH:4]=1

참가 물질

8

반응물 5

HCID 297MethaneHCID 5238Sodium IodideHCID 109652-Chloroethyl methyl sulfideHCID 11430Potassium CarbonateHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

생성물 1

HCID 124098Metoclopramide sulfide수율 32%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

A stirred mixture of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (10.0 g, 31.06 mmoles) (from Preparation No. 1A), anhydrous potassium carbonate (12.84 g, 93.16 mmoles), sodium iodide (4.66 g, 31.06 mmoles) and 2-chloroethyl methyl sulfide (3.70 ml, 4.10 g, 37.26 mmoles) in 60 ml of dry DMF was refluxed for 10 hours. The solvent was evaporated under reduced pressure and the dark semi-solid was partitioned between water and methylene chloride. Sodium hydroxide solution was added to bring the pH of the aqueous layer to 14. The mixture was shaken well and the layers were separated. The aqueous layer was extracted with 3 portions of methylene chloride. The combined organic solutions were dried over MgSO4 and evaporated. The solid obtained was dissolved in 100 ml of warm acetonitrile. The solution was treated with Darco G-60, filtered, evaporated to 30 ml, and stored at -15°. The solid was filtered to give 3.56 g (32%) of the title compound as off-white crystals, mp. 118°-120°.

후처리

  1. temperaturewas refluxed for 10 hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe dark semi-solid was partitioned between water and methylene chloride
  4. additionSodium hydroxide solution was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted with 3 portions of methylene chloride
  7. dry with materialThe combined organic solutions were dried over MgSO4
  8. customevaporated
  9. customThe solid obtained
  10. filtrationfiltered
  11. customevaporated to 30 ml
  12. customstored at -15°
  13. filtrationThe solid was filtered

출처 및 근거

ORD 기록
ord-33ae6709722d429cbd81ffe1cfda7c46
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04808624

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