2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Aminobenzo[b]thiophene-3-carboxamide

HRID 1919504Notes

Reaction equation

HRID 1919504 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH2:13])=[O:12].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([NH2:13])=[O:12]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 2902232-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

Product 1

HCID 122835332-Aminobenzo[b]thiophene-3-carboxamideYield 72.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.96 grams (10 mmol) of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide was slowly treated with 9.0 grams (40 mmol) DDQ in toluene at room temperature. The reaction was mixed at 40° C. for 15 hours, and monitored by GLC. The solvent was then removed under reduced pressure, and the residue was transferred to 10 ml of dichloromethane and filtered via Celite. The filtrate was purified by chromatography on silica gel, using dichloromethane and ethyl acetate (at an 8:2 ratio), yielding 1.4 grams (70% yield) of 2-aminobenzo[b]thiophene-3-carboxamide as yellow powder.

Workup

  1. additionThe reaction was mixed at 40° C. for 15 hours
  2. customThe solvent was then removed under reduced pressure
  3. filtrationfiltered via Celite
  4. customThe filtrate was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-408d1d56518345308b1b55cda332ce24
Source dataset
uspto-grants-2012_05
Patent number
US08168639B2

Reaction notes

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