Ammonia → 2-(3-Amino-1,1-dioxo-thietan-3-yl)acetamide

HRID 1480235Notes

Reaction equation

HRID 1480235 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.[NH3:16]>>[NH2:1][C:2]1([CH2:8][C:9]([NH2:16])=[O:11])[CH2:5][S:4](=[O:7])(=[O:6])[CH2:3]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 90202743Ethyl (3-amino-1,1-dioxido-3-thietanyl)acetate

Product 1

HCID 902138302-(3-Amino-1,1-dioxo-thietan-3-yl)acetamide

Conditions

Temperature
45 °C

Procedure

Ethyl 2-(3-amino-1,1-dioxo-thietan-3-yl)acetate (example 160c, 550 mg, 2.65 mmol) was dissolved in ammonia 7.0M in methanol (9 ml, 63.0 mmol) and the reaction flask was sealed (size of the flask was chosen to minimize the volume for gas expansion in order to minimize ammonia evaporation). The reaction was stirred at 45° C. for 2 days. Volatiles were removed in vacuo to yield a crude material (523 mg) containing a 4:1 ratio of amide:methyl ester. The crude material was used without any further purification; MS (ESI, m/z): 179.1 (M+H+).

Workup

  1. customthe reaction flask was sealed (size of the flask
  2. customammonia evaporation)
  3. customVolatiles were removed in vacuo

Sources & evidence

ORD record
ord-aecf33b051d94654aa170e8ac8ba3600
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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