Octanoyl chloride → 8-Chloro-N-(1-hydroxyoctylidene)dibenzo[b,f][1,4]oxazepine-10(11H)-carbohydrazonic acid

HRID 1729713Notes

Reaction equation

HRID 1729713 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(=O)(O)[O-].[Na+].[C:26](Cl)(=[O:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(#N)C>[C:26]([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:34])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 8124Octanoyl chlorideHCID 516892Sodium BicarbonateHCID 135604618-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazide

Product 1

HCID 2176068-Chloro-N-(1-hydroxyoctylidene)dibenzo[b,f][1,4]oxazepine-10(11H)-carbohydrazonic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.5 part of 8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine-10-carboxylic acid hydrazide and 19.6 parts of acetonitrile is added 0.298 part of sodium bicarbonate followed by 0.562 part of octanoyl chloride. The solution is stirred for 48 hours at room temperature, after which time the solvent is removed under reduced pressure and the resulting oil crystallized by trituration with cyclohexane. Recrystallization from cyclohexane yields 1-octanoyl-2-(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepine-10-carbonyl) hydrazine, melting at about 127°-129° and represented by the following structural formula ##SPC2##

Workup

  1. customafter which time the solvent is removed under reduced pressure
  2. customthe resulting oil crystallized by trituration with cyclohexane
  3. customRecrystallization from cyclohexane

Sources & evidence

ORD record
ord-12545d1267b04a989c74c31350c4b965
Source dataset
uspto-grants-1976_11
Patent number
US03989719

Reaction notes

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