Sodium Hydroxide → 6-bromo-N-(10-imidazol-1-yldecyl)benzo[cd]indol-2-amine

HRID 568496Notes

Reaction equation

HRID 568496 reaction equation
Cl.Cl.[N:3]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:7]=[CH:6][N:5]=[CH:4]1.[OH-].[Na+].C(O)C.O.[Br:25][C:26]1[C:27]2[C:28]3[C:32](=[CH:33][CH:34]=1)[N:31]=[C:30](S)[C:29]=3[CH:36]=[CH:37][CH:38]=2>C(O)C>[Br:25][C:26]1[C:27]2[C:28]3[C:32](=[CH:33][CH:34]=1)[N:31]=[C:30]([NH:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)[C:29]=3[CH:36]=[CH:37][CH:38]=2

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 19096565Water ethanolHCID 13171546610-(1H-imidazol-l-yl)decanamine, dihydrochlorideHCID 178527759HCID 178527759, compound

Product 1

HCID 1784192906-bromo-N-(10-imidazol-1-yldecyl)benzo[cd]indol-2-amineYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2.8 g of 10-(1H-imidazol-1-yl)decanamine, dihydrochloride was treated with 2 ml of 10N sodium hydroxide in an ethanol-water mixture giving the base derivative. To this base was added 25 ml of ethanol, 2.33 g of 6-bromo-benz[cd]indole-2-thiol and 3 g of mercuric acetate. The procedure of Example 1 was then followed, giving 2.8 g of the desired product, mp 115°-116° C.

Workup

  1. customgiving the base derivative

Sources & evidence

ORD record
ord-db56989a141a4068a05c7481a76e521f
Source dataset
uspto-grants-1988_03
Patent number
US04728663

Reaction notes

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