3-Amino-1-propanol → 3-{(dibenzo[b,e]-thiepin-11(6H)-yliden)-amino}-1-propanol

HRID 1287921Notes

Reaction equation

HRID 1287921 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.[NH2:17][CH2:18][CH2:19][CH2:20][OH:21]>O>[CH:1]1[C:11]2[C:10](=[N:17][CH2:18][CH2:19][CH2:20][OH:21])[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

Participants

4

Reactant 2

HCID 90863-Amino-1-propanolHCID 73741Dibenzo[b,e]thiepin-11(6H)-one

Product 1

HCID 215070363-{(dibenzo[b,e]-thiepin-11(6H)-yliden)-amino}-1-propanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30.0 G. of dibenzo[b,e]thiepin-11(6H)-one are heated to 180° C. with 300 ml. of 3-amino-1-propanol. The water formed and the excess amine are distilled off for 2 hours and the residue is then cooled, diluted with methylene chloride and washed several times with distilled water. The organic phase is dried over sodium sulfate and evaporated. After chromatographic purification over silica gel using toluene for the elution, there is obtained 3-{(dibenzo[b,e]-thiepin-11(6H)-yliden)-amino}-1-propanol.

Workup

  1. distillationthe excess amine are distilled off for 2 hours
  2. temperaturethe residue is then cooled
  3. additiondiluted with methylene chloride
  4. washwashed several times with distilled water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customevaporated
  7. customAfter chromatographic purification over silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-2972d6e10af0459d97dea6bc94ec7d93
Source dataset
uspto-grants-1976_10
Patent number
US03985895

Reaction notes

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