Tetrahydrofuran → HCID 178515336, compound

HRID 485463Notes

Reaction equation

HRID 485463 reaction equation
O1CCCC1.[Cl-].[Al+3].[Cl-].[Cl-].[C:10]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]2[C:22](=[O:23])[CH2:21][C:20]3[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=3[S:18][C:17]=2[CH:28]=1)#[N:11].[N-:29]=[N+:30]=[N-:31].[Na+]>O>[NH:29]1[C:10]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]3[C:22](=[O:23])[CH2:21][C:20]4[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=4[S:18][C:17]=3[CH:28]=2)=[N:11][N:31]=[N:30]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 202702303-Cyanomethyl-10,11-dihydro-11-oxodibenzo[b,f]thiepin

Product 1

HCID 178515336HCID 178515336, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add to 25 cc. of tetrahydrofuran cooled in an ice bath 1.59 gm. (11.9 mmole) of aluminum chloride, 1.33 gm. (5.25 mmole) of 3-cyanomethyl-10,11-dihydro-11-oxodibenzo[b,f]thiepin and 1.55 gm. (23.8 mmole) of sodium azide. Reflux the mixture for 19 hours, cool, dilute with water and acidify. Extract the mixture into ethyl acetate and evaporate. Triturate the residue in ether and separate the title product by filtration.

Workup

  1. additionAdd to 25 cc
  2. temperatureReflux the mixture for 19 hours
  3. temperaturecool
  4. extractionExtract the mixture into ethyl acetate
  5. customevaporate
  6. customTriturate the residue in ether
  7. customseparate the title product
  8. filtrationby filtration

Sources & evidence

ORD record
ord-7c4e25b67a7a4dcc8b4ba67bdf143ab1
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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