Sodium Azide → 6(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 1679628Notes

Reaction equation

HRID 1679628 reaction equation
[C:1]1([C:7]([NH:20][CH:21]2[C:31](=[O:32])[N:23]3[CH:24]([C:29]#[N:30])[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:33]=[N+:34]=[N-:35].[Na+].Cl.CN1CCCCC1>C(Cl)(Cl)Cl>[C:1]1([C:7]([NH:20][CH:21]2[C:31](=[O:32])[N:23]3[CH:24]([C:29]4[NH:35][N:34]=[N:33][N:30]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 205378Piperidine, 1-methyl-, hydrochlorideHCID 70604455HCID 70604455, compound

Product 1

HCID 1784319216(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 6-triphenylmethylamino-2,2-dimethyl-3-cyanopenam (10 g. 0.0193 mole) sodium azide (7.41 g., 0.114 mole), N-methylpiperidine hydrochloride (3.39 g., 0.025 mole) and chloroform (100 ml.) is refluxed for four hours in a round-bottomed flask equipped with stirrer, condenser, and drying tube. The reaction mixture is then cooled and water (300 ml.) and chloroform (100 ml.) added. The mixture is thoroughly mixed, the chloroform layer separated and washed successively with 1N hydrochloric acid (100 ml.) and saturated brine (100 ml.). It is then filtered quickly through anhydrous sodium sulfate and concentrated under reduced pressure to about 75 ml. Hexane (20 ml.) is added to the concentrate to precipitate the product as white crystals. The crystals are recovered by filtration, washed with 20% hexane-methylene chloride (50 ml.) and dried in vacuo at room temperature. Yield = 2.7 g. (29.6%) m.p. 133°-136° C.

Workup

  1. temperatureis refluxed for four hours in a round-bottomed flask
  2. customequipped with stirrer, condenser
  3. customdrying tube
  4. temperatureThe reaction mixture is then cooled
  5. additionwater (300 ml.) and chloroform (100 ml.) added
  6. additionThe mixture is thoroughly mixed
  7. customthe chloroform layer separated
  8. washwashed successively with 1N hydrochloric acid (100 ml.) and saturated brine (100 ml.)
  9. filtrationIt is then filtered quickly through anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure to about 75 ml
  11. additionHexane (20 ml.) is added to the
  12. concentrationconcentrate
  13. customto precipitate the product as white crystals
  14. filtrationThe crystals are recovered by filtration
  15. washwashed with 20% hexane-methylene chloride (50 ml.)
  16. customdried in vacuo at room temperature

Sources & evidence

ORD record
ord-7b2aa4cc354343bfa2112b4c0b6f6450
Source dataset
uspto-grants-1978_03
Patent number
US04081455

Reaction notes

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