Dimethylformamide → Benzo[b]thiophene-2-carbonyl Chloride

HRID 1479900Notes

Reaction equation

HRID 1479900 reaction equation
[CH:1]1[CH:6]=[C:5]2[CH:7]=[C:8]([C:10]([OH:12])=O)[S:9][C:4]2=[CH:3][CH:2]=1.S(Cl)([Cl:15])=O.CN(C=O)C>C1(C)C=CC=CC=1>[S:9]1[C:8]([C:10]([Cl:15])=[O:12])=[CH:7][C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][C:4]1=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 95864Benzo(b)thiophene-2-carboxylic acid

Product 1

HCID 142384Benzo[b]thiophene-2-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thianaphthene-2-carboxylic acid (356.42 mg, 2 mmol) was suspended in dry toluene (6 mL), thionyl chloride (4.4 mL, 60 mmol) and DMF (0.05 mL) were added at room temperature, and then the mixture was refluxed 8 h.4 The volatiles were removed at reduced pressure gave benzo[b]thiophene-2-carbonyl chloride as a yellow power. Purified by flash chromatography on silica gel, using ethyl acetate/hexane (1:9) as eluent, give 3 as a white power (393.64 mg, 94.9%). Spectral data were in accordance with those published. 1H-NMR (300 MHz, CDCl3): δ 8.31 (s, 1H), 7.04-7.89 (m, 2H), 7.60-7.46 (m, 2H. 13C NMR (300 MHz, CDCl3): δ 161.14, 144.07, 138.05, 136.59, 135.89, 128.75, 126.68, 125.66, 122.91.

Workup

  1. temperaturethe mixture was refluxed 8 h
  2. custom4 The volatiles were removed at reduced pressure

Sources & evidence

ORD record
ord-00f5278006be471ab9a630d5a0c3164a
Source dataset
uspto-grants-2016_08
Patent number
US09409880B2

Reaction notes

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