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

HRID 1735111Notes

Reaction equation

HRID 1735111 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-dc9b21c0ec074569b51db4d9f7fb9792
Source dataset
uspto-grants-1996_07
Patent number
US05536721

Reaction notes

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