Tetrahydrofuran → N,N-diethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine

HRID 1287925Notes

Reaction equation

HRID 1287925 reaction equation
[CH2:1]([N:3]([CH2:23][CH3:24])[CH2:4][CH2:5][CH2:6][NH:7][CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][S:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[CH3:2].O1CCCC1.Cl[O-].[Na+]>O>[CH2:23]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][N:7]=[C:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][S:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[CH3:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21507033N,N-diethyl-N'-{6,11-dihydro-dibenzo[b,e]thiepin-11-yl}-1,3-propanediamineHCID 23665760Sodium Hypochlorite

Product 1

HCID 21507028N,N-diethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.3 G. of N,N-diethyl-N'-{6,11-dihydro-dibenzo[b,e]thiepin-11-yl}-1,3-propanediamine are dissolved in 50 ml. of absolute tetrahydrofuran and treated dropwise, while stirring, with 6 ml. of 14% aqueous sodium hypochlorite solution. The mixture is stirred at 40°-50° C. for 4 hours, cooled and mixed with 100 ml. of water. The organic phase is extracted with ether. The ether extract is dried over sodium sulfate and evaporated under reduced pressure. The residue is purified by chromatography over aluminum oxide using toluene for the elution. There is obtained N,N-diethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine which is taken up in acetone and treated with a solution of 0.4 g. of oxalic acid in 10 ml. of absolute acetone. There is thus obtained N,N-diethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine oxalate of melting point 130°-133° C.

Workup

  1. stirringThe mixture is stirred at 40°-50° C. for 4 hours
  2. temperaturecooled
  3. additionmixed with 100 ml
  4. extractionThe organic phase is extracted with ether
  5. extractionThe ether extract
  6. dry with materialis dried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue is purified by chromatography over aluminum oxide
  9. washfor the elution

Sources & evidence

ORD record
ord-5951698890214e84b24b27598738af2f
Source dataset
uspto-grants-1976_10
Patent number
US03985895

Reaction notes

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