Bromine → HCID 13084274, compound

HRID 1164323Notes

Reaction equation

HRID 1164323 reaction equation
[S:1]=[C:2]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:8]3[C:9]=2[C:4](=[CH:5][CH:6]=[CH:7]3)[N:3]1[CH2:14][C:15]([OH:17])=[O:16].[Br:18]Br>C(O)(=O)C>[Br:18][C:7]1[C:8]2[C:9]3[C:4](=[CH:5][CH:6]=1)[N:3]([CH2:14][C:15]([OH:17])=[O:16])[C:2](=[S:1])[C:10]=3[CH:11]=[CH:12][CH:13]=2

Participants

4

Reactant 2

HCID 24408BromineHCID 3069842Benz(cd)indole-1(2H)-acetic acid, 2-thioxo-

Product 1

HCID 13084274HCID 13084274, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

To a suspension of 2-thioxo-benz[cd]indole-1(2H)-acetic acid (4.2 g, 17.26 mmol, described in Example 6), in glacial acetic acid (80 mL) was added a solution of bromine (3.59 g, 22.44 mmol) in glacial acetic acid (20 mL) in two portions with mechanical stirring within one hour. After initial clearing of the suspension, a heavy precipitate was formed. More acetic acid (60 mL) was added in order to make stirring more efficient. The mixture was filtered and the precipitate was washed twice with water (150 mL), dried, crystallized from ethanol-water giving 4.7 g in two crops and recrystallized from methanol to give 3.0 g of the title compound, identical in all respects to that prepared in Example 6.

Workup

  1. customAfter initial clearing of the suspension, a heavy precipitate was formed
  2. stirringto make stirring more efficient
  3. filtrationThe mixture was filtered
  4. washthe precipitate was washed twice with water (150 mL)
  5. customdried
  6. customcrystallized from ethanol-water giving 4.7 g in two crops
  7. customrecrystallized from methanol

Sources & evidence

ORD record
ord-cbfef29a390e4c1eac9e45e23170dc9d
Source dataset
uspto-grants-1983_01
Patent number
US04369188

Reaction notes

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