Water → Methyl 8-methyl-5-nitrothieno[2,3-b]indole-2-carboxylate

HRID 1957215Notes

Reaction equation

HRID 1957215 reaction equation
Cl[C:2]1[N:3]([CH3:16])[C:4]2[C:9]([C:10]=1[CH:11]=O)=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2.C([O-])([O-])=O.[K+].[K+].[SH:23][CH2:24][C:25]([O:27][CH3:28])=[O:26].O>CO>[CH3:16][N:3]1[C:4]2[C:9](=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2)[C:10]2[CH:11]=[C:24]([C:25]([O:27][CH3:28])=[O:26])[S:23][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 108238742-Chloro-1-methyl-5-nitroindole-3-carbaldehyde

Product 1

HCID 19068989Methyl 8-methyl-5-nitrothieno[2,3-b]indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.4 g of (66) was added to a slurry of excess K2CO3 in 100 ml of MeOH. 2 ml of methyl 2-mercaptoacetate was added and the mixture left with stirring overnight. Addition of water precipitated the product, which was washed with MeOH and water to give 640 mg of (67). M. p. 269°-71° C.

Workup

  1. waitthe mixture left
  2. customprecipitated the product, which
  3. washwas washed with MeOH and water

Sources & evidence

ORD record
ord-777f1d48539046ee8810b748702d8889
Source dataset
uspto-grants-1998_07
Patent number
US05783575

Reaction notes

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