Methanol → 2-(3-amino-1,1-dioxo-thietan-3-yl)-N-methyl-acetamide

HRID 1480334Notes

Reaction equation

HRID 1480334 reaction equation
[NH2:1][C:2]1([CH2:8][C:9]([O:11]CC)=O)[CH2:5][S:4](=[O:7])(=[O:6])[CH2:3]1.CO.[CH3:16][NH2:17]>>[NH2:1][C:2]1([CH2:8][C:9]([NH:17][CH3:16])=[O:11])[CH2:5][S:4](=[O:7])(=[O:6])[CH2:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 6329MethylamineHCID 90202743Ethyl (3-amino-1,1-dioxido-3-thietanyl)acetate

Product 1

HCID 902149512-(3-amino-1,1-dioxo-thietan-3-yl)-N-methyl-acetamideYield 99%

Conditions

Temperature
45 °C

Procedure

ethyl 2-(3-amino-1,1-dioxo-thietan-3-yl)acetate (example 160c, 548 mg, 2.64 mmole) was dissolved in a solution 2.0M of methylamine in methanol (19.8 mL, 39.7 mmole) and the reaction mixture was stirred at 45° C. overnight. Removal of volatiles in vacuo yielded the title compound (505 mg, 99%) as crude light brown oil which was used without any further purification; MS (ESI, m/z): 193.1 (M+H+).

Workup

  1. customRemoval of volatiles in vacuo

Sources & evidence

ORD record
ord-9fc7c4fea7004a0c9d0b15e5f1b5e251
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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