Ethanol → 7-Nitro-2-(1,3-thiazol-2-yl)-1H-indole

HRID 1851367Notes

Reaction equation

HRID 1851367 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13](=[S:15])[NH2:14])=[CH:9]2)([O-:3])=[O:2].Br[CH2:17][CH:18](OCC)OCC.C(O)C.CN(C)C(=O)C>O>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:15][CH:17]=[CH:18][N:14]=1)=[CH:9]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 31374DimethylacetamideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 579018667-nitro-1H-indole-2-carbothioamide

Product 1

HCID 579018457-Nitro-2-(1,3-thiazol-2-yl)-1H-indoleYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-nitro-1H-indole-2-carbothioamide (2.06 g), 2-bromo-1,1-diethoxyethane (3.67 g), ethanol (10 mL) and N,N-dimethylacetamide (10 mL) was stirred at 100° C. for 4 hr. To the reaction mixture was added water, and the resulting crystals were filtrated, washed with water and hexane, and dried to give the title compound (2.21 g, yield 97%) as yellow crystals. melting point 130-131° C.

Workup

  1. filtrationthe resulting crystals were filtrated
  2. washwashed with water and hexane
  3. customdried

Sources & evidence

ORD record
ord-09311367c773465fb7b47a642b8d008a
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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