HCID 13084267, compound → HCID 13084274, compound

HRID 1164322Notes

Reaction equation

HRID 1164322 reaction equation
[Br:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14]CC)=[O:13])[C:6](=[S:17])[C:5]=3[CH:18]=[CH:19][CH:20]=2>CO.[OH-].[Na+]>[Br:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6](=[S:17])[C:5]=3[CH:18]=[CH:19][CH:20]=2

Participants

4

Reactant 1

HCID 13084267HCID 13084267, compound

Product 1

HCID 13084274HCID 13084274, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of 6-bromo-2-thioxo-benz[cd]indole-1(2H)-acetic acid, ethyl ester (2.5 g, 7.1 mmol, described in Example 5) in methanol (70 mL) and 2 N aqueous sodium hydroxide (5.3 mL) was stirred at room temperature for 2 days and evaporated. The residue was dissolved in water (300 mL, with slight warming), and the solution was acidified. The precipitate was collected by filtration, dried, and crystallized from ethanol-water to give the title compound (2.05 g): mp 253° C. (245° C. darkening); Anal. Calcd for C13H8BrNO2S: C, 48.46% H, 2.50% N, 4.35% and Found: C, 48.32% H, 2.62% N, 4.38%; IR (mineral oil) 3100, and 1715 cm-1 ; UV max (methanol) 436 (ε12,830), 361 (4680), 342 (3130), 311 (8140), 302 (sh, 7950), and 273 nm (24,160); NMR (DMSO-d6)δ 5.08 (s, 2H), 7.30 (d, 1H), 7.90 (d, 1H), and 8.00 (m, 3 H).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water (300 mL, with slight warming)
  3. filtrationThe precipitate was collected by filtration
  4. customdried
  5. customcrystallized from ethanol-water

Sources & evidence

ORD record
ord-a4915999415643f5a139cc3b23ef5abc
Source dataset
uspto-grants-1983_01
Patent number
US04369188

Reaction notes

Loading…