Oxalyl chloride → 1,3-BENZOTHIAZOLE-6-CARBONYL CHLORIDE

HRID 2280294Notes

Reaction equation

HRID 2280294 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([OH:12])=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.C(Cl)(=O)C([Cl:16])=O>C(Cl)Cl.CN(C)C=O>[S:1]1[C:5]2[CH:6]=[C:7]([C:10]([Cl:16])=[O:12])[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 601670Benzothiazole-6-carboxylic acid

Product 1

HCID 122080221,3-BENZOTHIAZOLE-6-CARBONYL CHLORIDEYield 150.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

Under a nitrogen atmosphere, benzothiazole-6-carboxylic acid (1.014 g, 5.6 mmol) was dissolved in methylene chloride (25 mL). Five drops of N,N-dimethylforamide was added. Oxalyl chloride (0.5 mL, 5.6 mmol) was slowly added. After 2 hrs, the reaction was heated to 30° C. for 16 hrs. The reaction was concentrated in vacuo to yield benzothiazole-6-carbonyl chloride (19A) (1.665 g, quant., light yellow powder).

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-aa27aa48828f41f398d914f3d798210f
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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