Toluene → HCID 67094194, compound

HRID 1881181Notes

Reaction equation

HRID 1881181 reaction equation
[OH:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([OH:12])=O)[S:7][C:6]=2[C:13]=1[N+:14]([O-:16])=[O:15].S(Cl)(Cl)=O.[C:23]1([CH3:29])C=CC=CC=1>CN(C)C=O>[OH:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([N:14]3[CH2:29][CH2:23][O:1][CH2:2][CH2:13]3)=[O:12])[S:7][C:6]=2[C:13]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 67094379HCID 67094379, compound

Product 1

HCID 67094194HCID 67094194, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
80 °C

Procedure

6-Hydroxy-5-methoxy-7-nitro-benzo[b]thiophene-2-carboxylic acid (2.7 g) was dissolved in toluene (45 ml). Thionyl chloride (1.2 ml) and N,N-dimethylformamide (4 drops) were added. The solution was stirred at 80° C. for two hours and after that it was evaporated. The residue was dissolved into dichloromethane (45 ml) and morpholine (1.4 ml) and triethylamine (1.2 ml) added. The reaction solution was stirred at room temperature overnight. The solution of water and 2M HCl was added to the solution. The solid was washed with water and dried under vacuum.

Workup

  1. customafter that it was evaporated
  2. dissolutionThe residue was dissolved into dichloromethane (45 ml) and morpholine (1.4 ml) and triethylamine (1.2 ml)
  3. additionadded
  4. stirringThe reaction solution was stirred at room temperature overnight
  5. additionThe solution of water and 2M HCl was added to the solution
  6. washThe solid was washed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-8adb995ad8004ee08d47dd5c88027626
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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