Diethyl Ether → HCID 13606573, compound

HRID 977975Notes

Reaction equation

HRID 977975 reaction equation
C(C([NH:10][C:11]1[CH:30]=[CH:29][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][C:19](=[O:22])[C:18](=[C:23]3[S:27][CH:26]=[CH:25][S:24]3)[C:17]2=[O:28])=[CH:13][CH:12]=1)=O)C1C=CC=CC=1.[BrH:31].C(O)(=O)C.CCOCC>C(O)(=O)C>[BrH:31].[NH2:10][C:11]1[CH:30]=[CH:29][C:14]([CH2:15][N:16]2[CH2:21][CH2:20][C:19](=[O:22])[C:18](=[C:23]3[S:24][CH:25]=[CH:26][S:27]3)[C:17]2=[O:28])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 20204018HCID 20204018, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 13606573HCID 13606573, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(p-(N-Benzylcarbonylamino)benzyl)-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine (100 mg) is dissolved in acetic acid (2 ml), and a 25% HBr-acetic acid solution (0.5 ml) is added thereto. The mixture is stirred at room temperature for 40 minutes, and then at 40°-50° C. for one hour. After cooling the mixture, ether is added to the mixture. The precipitated crystals are collected by filtration, and recrystallized from a mixture of methanol and ether to give 1-(p-aminobenzyl)-3-(1,3-dithiol-2-ylidene)-2,4-dioxopiperidine hydrobromide (70 mg, 79.3%) as pale yellow needles, m.p. 210°-214° C. (decomp.).

Workup

  1. waitat 40°-50° C. for one hour
  2. additionis added to the mixture
  3. filtrationThe precipitated crystals are collected by filtration
  4. customrecrystallized from a mixture of methanol and ether

Sources & evidence

ORD record
ord-102a95fff05a4530a7126131c04dad02
Source dataset
uspto-grants-1987_05
Patent number
US04663319

Reaction notes

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