Dichloromethane → 2,1,3-Benzothiadiazole, 4,7-diethynyl-

HRID 1176177Notes

Reaction equation

HRID 1176177 reaction equation
C[Si]([C:5]#[C:6][C:7]1[C:15]2[C:11](=[N:12][S:13][N:14]=2)[C:10]([C:16]#[C:17][Si](C)(C)C)=[CH:9][CH:8]=1)(C)C.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>CO>[C:16]([C:10]1[C:11]2[C:15](=[N:14][S:13][N:12]=2)[C:7]([C:6]#[CH:5])=[CH:8][CH:9]=1)#[CH:17]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 12090793HCID 12090793, compound

Product 1

HCID 120907942,1,3-Benzothiadiazole, 4,7-diethynyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4,7-Bis(trimethylsilylethynyl)benzo[c][1,2,5]thiadiazole (0.126 g, 3.83×10−4 mol), K2CO3 (0.214 g, 1.55×10−3 mol), CH2Cl2 (5.0 ml) and MeOH (5.0 ml) were added to a 100-ml round-bottom flask. The reaction mixture was stirred at room temperature for 2.5 h under Ar. The reaction mixture was fdtered and the solvent was evaporated. The residue was chromatographed on short silica gel column with CH2Cl2 as the eluent. Yield=0.0663 g (94% based on 0.126 g of 4,7-bis(trimethylsilylethynyl)benzo[c][1,2,5]thiadiazole). 1H NMR (300 MHz, CDCl3): δ 7.78 (s, 2H, Ph-H), 3.70 (s, 2H, ethynyl-H). CI MS m/z: 184.010 (M+) (calcd 184.010).

Workup

  1. customthe solvent was evaporated
  2. customThe residue was chromatographed on short silica gel column with CH2Cl2 as the eluent

Sources & evidence

ORD record
ord-b2b0d017c5a24656946fe2ccf65cb600
Source dataset
uspto-grants-2010_11
Patent number
US07842758B2

Reaction notes

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