Sodium Hydroxide → HCID 9951823, compound

HRID 1089743Notes

Reaction equation

HRID 1089743 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12]4[C:13](=[CH:18][CH:19]=[CH:20][C:11]=4[C:10]2=S)[CH:14]=[CH:15][CH:16]=3)=[CH:4][CH:3]=1.[N:22]1([CH2:27][CH2:28][CH2:29][NH2:30])[CH:26]=[CH:25][N:24]=[CH:23]1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12]4[C:13](=[CH:18][CH:19]=[CH:20][C:11]=4[C:10]2=[N:30][CH2:29][CH2:28][CH2:27][N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)[CH:14]=[CH:15][CH:16]=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 787361H-Imidazole-1-propanamineHCID 15023410HCID 15023410, compound

Product 1

HCID 9951823HCID 9951823, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.5 g of 1-[(4-methylphenyl)methyl]benz[cd]indole-2(1H)-thione (Ca) and 1.2 g of 1H-imidazole-1-propanamine in 200 ml of ethyl alcohol is stirred and heated. A 2.7 g portion of mercuric acetate is added, the mixture is stirred at reflux for 6 hours, cooled to room temperature and treated with 2N sodium hydroxide (pH 9). After filtering the solution through diatomaceous earth, the reaction is concentrated in vacuo. The resulting oil is dissolved in dichloromethane, washed neutral with water, dried over sodium sulfate and concentrated in vacuo. The crystalline residue is recrystallized from dichloromethane/hexane giving 2.2 g of the desired product, mp. 94°-95° C.

Workup

  1. temperatureheated
  2. stirringthe mixture is stirred
  3. temperatureat reflux for 6 hours
  4. filtrationAfter filtering the solution through diatomaceous earth
  5. concentrationthe reaction is concentrated in vacuo
  6. dissolutionThe resulting oil is dissolved in dichloromethane
  7. washwashed neutral with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crystalline residue is recrystallized from dichloromethane/hexane giving 2.2 g of the desired product, mp. 94°-95° C.

Sources & evidence

ORD record
ord-a28220af546d41b19672a6a817b50fd6
Source dataset
uspto-grants-1992_01
Patent number
US05079247

Reaction notes

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