Dodecanoyl chloride → HCID 21505557, compound

HRID 1287616Notes

Reaction equation

HRID 1287616 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH2:9][CH:8]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]3)[C:7]=2[CH:27]=1)[CH3:2].[C:28](Cl)(=[O:40])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].C(O)(=O)/C=C\C(O)=O>C1C=CC=CC=1.C(Cl)(Cl)Cl.CC(C)=O.[OH-].[NH4+]>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]2[S:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[CH2:9][CH:8]([N:17]3[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][CH2:25][O:26][C:28](=[O:40])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[CH2:21][CH2:22]3)[C:7]=2[CH:27]=1)[CH3:2]

Participants

8

Reactant 3

HCID 8166Dodecanoyl chlorideHCID 114710HCID 114710, compoundHCID 444266Maleic Acid

Product 1

HCID 21505557HCID 21505557, compound

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 241BenzeneSolventHCID 6212ChloroformSolventHCID 14923Ammonium HydroxideSolvent

Procedure

In accordance with the general method described in the foregoing Examples, 10.15 grams of 8-ethyl-10-[4-(3-hydroxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin was reacted with a solution of 12.5 grams of lauroyl chloride (dodecanoyl chloride) in a mixture of 60 milliliters of benzene and 20 milliliters of chloroform. By adding a solution of 6.15 grams of maleic acid in 60 milliliters of acetone to the crude product, 14.0 grams of 8-ethyl-10-[4-(3-dodecanoyloxypropyl)piperazino]-10,11-dihydrodibenzo[b,f]thiepin di(hydrogen maleate) was recovered. The salt, after recrystallization from acetone, had a melting point of 126°-128°C. Its elemental analysis corresponded to the empirical formula C43H60N2O10S. The free base was obtained in the form of a colorless very viscous oil which was very soluble in vegetable oils by dissolving the salt in a dilute aqueous ammonium hydroxide solution and extracting the resulting solution with benzene.

Workup

  1. customwas recovered
  2. customThe salt, after recrystallization from acetone
  3. customThe free base was obtained in the form of a colorless very viscous oil which
  4. extractionextracting the resulting solution with benzene

Sources & evidence

ORD record
ord-f0ba1e7c01aa4b7aad538a650eb960ba
Source dataset
uspto-grants-1976_10
Patent number
US03985750

Reaction notes

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