Hydrochloric Acid → 2,7-Bis(4-aminobutyryl)thioxanthene Dihydrochloride

HRID 1076898

Reaction equation

HRID 1076898 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][C:9]([C:11]2[CH:24]=[CH:23][C:22]3[S:21][C:20]4[C:15](=[CH:16][C:17]([C:25](=[O:40])[CH2:26][CH2:27][CH2:28][N:29]5C(=O)C6=CC=CC=C6C5=O)=[CH:18][CH:19]=4)[CH2:14][C:13]=3[CH:12]=2)=[O:10])C(=O)C2=CC=CC=C12.C1(=O)N(CCCC([Cl:57])=O)C(=O)C2=CC=CC=C12.C1C2CC3C(=CC=CC=3)SC=2C=CC=1.[ClH:78]>C(O)(=O)C>[ClH:57].[ClH:78].[NH2:29][CH2:28][CH2:27][CH2:26][C:25]([C:17]1[CH:18]=[CH:19][C:20]2[S:21][C:22]3[C:13](=[CH:12][C:11]([C:9](=[O:10])[CH2:8][CH2:7][CH2:6][NH2:5])=[CH:24][CH:23]=3)[CH2:14][C:15]=2[CH:16]=1)=[O:40]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 67495ThioxantheneHCID 5948864-(1,3-Dioxoisoindolin-2-yl)butanoyl chlorideHCID 21538549HCID 21538549, compound

Product 1

HCID 215385232,7-Bis(4-aminobutyryl)thioxanthene Dihydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,7-Bis(4-phthalimidobutyryl)thioxanthene, prepared from 4-phthalimidobutyryl chloride and thioxanthene by the method of S.S. Cheng et al., J. Med. Chem. 9, 945 (1966), is treated with hot glacial acetic acid after which concentrated HCl is added gradually with stirring. The mixture is heated to reflux for 24 hours with a constant stream of HCl gas passing through the mixture. The reaction mixture is stirred and refluxed for an additional 24 hours, cooled, and the product worked up in the usual manner.

Workup

  1. additionis added gradually
  2. temperatureThe mixture is heated
  3. stirringThe reaction mixture is stirred
  4. temperaturerefluxed for an additional 24 hours
  5. temperaturecooled

Sources & evidence

ORD record
ord-32bbde71d22946ac9780e9de7f260c7f
Source dataset
uspto-grants-1976_05
Patent number
US03957988

Linked notes

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