Acetic Anhydride → 2-(1-Cyano-2-methoxypropenyl)benzothiazole-5-sulfonic acid methylamide

HRID 407299Notes

Reaction equation

[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH2:14][C:15]#[N:16])=[N:11][C:10]=2[CH:17]=1)(=[O:5])=[O:4].[C:18]([O:21][C:22](=O)C)(=O)[CH3:19]>>[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([C:14]([C:15]#[N:16])=[C:18]([O:21][CH3:22])[CH3:19])=[N:11][C:10]=2[CH:17]=1)(=[O:4])=[O:5]

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 18788000HCID 18788000, compound

Product 1

HCID 667682252-(1-Cyano-2-methoxypropenyl)benzothiazole-5-sulfonic acid methylamideYield 83%

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-cyanomethylbenzothiazole-5-sulfonic acid methylamide (120 mg, 0.45 mmol) and trimethyl orthoracetate (270 mg, 2.2 mmol) in acetic anhydride (2 mL) was heated at 100° C. for 5 hrs. The reaction mixture was cooled to room temperature. The resulting precipitate was isolated by filtration to yield 120 mg (83%) of 2-(1-cyano-2-methoxypropenyl)benzothiazole-5-sulfonic acid methylamide. The product was used in the subsequent step without further purification. MS (m/z, ES+): 324 (M+1, 100%).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe resulting precipitate was isolated by filtration

Sources & evidence

ORD record: ord-fd7dccf0bf9c4daf9f717716dcea1472
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754233B2

Reaction notes

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