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

HRID 1287927Notes

Reaction equation

HRID 1287927 reaction equation
[CH:1]1[C:11]2[C:10](=O)[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[CH2:7][S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:17]([NH:19][CH2:20][CH2:21][CH2:22][NH2:23])[CH3:18].C1(C)C=CC=CC=1>[Ti](Cl)(Cl)(Cl)Cl.O>[CH2:17]([NH:19][CH2:20][CH2:21][CH2:22][N:23]=[C:10]1[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[CH2:7][S:6][C:5]2[CH:4]=[CH:3][CH:2]=[CH:1][C:11]1=2)[CH3:18]

Participants

6

Reactant 3

HCID 1140TolueneHCID 73741Dibenzo[b,e]thiepin-11(6H)-oneHCID 82727N-Ethyl-1,3-propanediamine

Product 1

HCID 21507035N-ethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolvent

Procedure

9.1 g. of dibenzo[b,e]thiepin-11(6H)-one are mixed, while stirring, with 40 g. of N-ethyl-1,3-propanediamine and 250 ml. of absolute toluene and treated dropwise at 0° C. with 8.8 ml. of titanium tetrachloride. The reaction mixture is stirred at room temperature for 18 hours, then cooled and hydrolyzed with 250 ml. of water. The resulting suspension is filtered through diatomaceous earth and the aqueous phase is extracted with toluene. The combined toluene extracts are dried over sodium sulfate and evaporated under reduced pressure. Raw N-ethyl-N'-{dibenzo[b,e]thiepin-11(6H)-ylidene}-1,3-propanediamine is obtained which can be used directly in the above reaction.

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 18 hours
  2. temperaturecooled
  3. filtrationThe resulting suspension is filtered through diatomaceous earth
  4. extractionthe aqueous phase is extracted with toluene
  5. dry with materialThe combined toluene extracts are dried over sodium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9e96ac78ae434e3ba597131998d98b9f
Source dataset
uspto-grants-1976_10
Patent number
US03985895

Reaction notes

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