반응 #1817505

반응 방정식

6-triphenylmethylamino-2,2-dimethyl-3-carbamylpenam

pyridine

Phosgene

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product

수율 67.3%

6-Triphenylmethylamino-2,2-Dimethyl-3-Cyanopenam

수율 67.3%

용매

chloroform

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture is stirred at 5° C. for ten minutes after which the cooling bath
2. 2
   기타is removed
3. 3
   온도to warm to room temperature
4. 4
   workup.STIRRINGIt is stirred for 30 minutes
5. 5
   세척washed successively with water (300 ml.), 1N hydrochloric acid (300 ml.), and water (300 ml.)
6. 6
   건조The chloroform solution is dried (MgSO4)
7. 7
   workup.ADDITIONtreated with activated charcoal
8. 8
   여과filtered through diatomaceous earth
9. 9
   농축The filtrate is concentrated to reduced pressure
10. 10
    세척).The methylene chloride solution is washed successively with 1N hydrochloricacid (150 ml.) and water (300 ml.)
11. 11
    기타dried
12. 12
    여과The dried solution is then filtered
13. 13
    농축concentrated under reduced pressure

실험 절차

A mixture of 6-triphenylmethylamino-2,2-dimethyl-3-carbamylpenam (11.01g., 0.024 mole), dry pyridine (4.9g., 0.062 mole) and dry chloroform (250 ml.)is stirred for five minutes and the resulting solution cooled to 0° C. in a wet ice/acetone bath. Phosgene (8.8 ml. of 3.41 molar solution in chloroform) is added by means of a syringe. The reaction mixture is stirred at 5° C. for ten minutes after which the cooling bath is removed and the reaction mixture allowed to warm to room temperature. It is stirred for 30 minutes and then washed successively with water (300 ml.), 1N hydrochloric acid (300 ml.), and water (300 ml.). The chloroform solution is dried (MgSO4), treated with activated charcoal, and filtered through diatomaceous earth. The filtrate is concentrated to reduced pressure and the residue taken up in methylene chloride (450 ml.).The methylene chloride solution is washed successively with 1N hydrochloricacid (150 ml.) and water (300 ml.) and then dried using anhydrous sodium sulfate. The dried solution is then filtered and concentrated under reduced pressure to give the product as a golden foam (7.1 g., 67.3%).

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