Triethylamine → HCID 53790624, compound

HRID 1730264Notes

Reaction equation

HRID 1730264 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]2[O:6][C:7]3[CH:18]=[CH:17][CH:16]=[CH:15][C:8]=3[CH2:9][N:10]([C:11]([NH:13][NH2:14])=[O:12])[C:4]=2[CH:3]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:37])[CH:29]=[CH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1C=CC=CC=1>[C:28]([NH:14][NH:13][C:11]([N:10]1[CH2:9][C:8]2[CH:15]=[CH:16][CH:17]=[CH:18][C:7]=2[O:6][C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][C:4]1=2)=[O:12])(=[O:37])[CH:29]=[CH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660233-Phenylprop-2-enoyl chlorideHCID 135604618-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazide

Product 1

HCID 53790624HCID 53790624, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution containing 1.45 parts of 8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine-10-carboxylic acid hydrazide dissolved in 50 parts by volume of benzene is added successively0.7 part by volume of triethylamine and 0.81 part of cinnamoyl chloride. The resulting reaction mixture is stirred at room temperature for about 48hours, then is washed successively with dilute hydrochloric acid, dilute aqueous sodium hydroxide, water and saturated aqueous sodium chloride. Drying over anhydrous sodium sulfate followed by removal of the solvent bydistillation under reduced pressure affords a residue, which is purified byadsorption on a silicic acid chromatographic column and elution with ethyl acetate-benzene mixtures. The 10% acetate in benzene eluate, upon removal of the solvents, affords 1-cinnamoyl-2-(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine-10-carbonyl)hydrazine.

Workup

  1. customThe resulting reaction mixture
  2. washis washed successively with dilute hydrochloric acid, dilute aqueous sodium hydroxide, water and saturated aqueous sodium chloride
  3. dry with materialDrying over anhydrous sodium sulfate
  4. customfollowed by removal of the solvent bydistillation under reduced pressure
  5. customaffords a residue, which
  6. customis purified byadsorption on a silicic acid chromatographic column and elution with ethyl acetate-benzene mixtures
  7. customThe 10% acetate in benzene eluate, upon removal of the solvents

Sources & evidence

ORD record
ord-aa69d35cd6e6491aaf7b7105b3da845c
Source dataset
uspto-grants-1976_11
Patent number
US03992375

Reaction notes

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