Ammonia → Thietan-3-amine

HRID 1470565Notes

Reaction equation

HRID 1470565 reaction equation
[N:1]1[CH:6]=[CH:5]C=[CH2+]C=1.[C:7]1([CH3:17])[CH:12]=[CH:11][C:10]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.S1CCC1.[NH3:22]>CO>[S:13]1[CH2:5][CH:6]([NH2:1])[CH2:10]1.[S:13]([C:10]1[CH:11]=[CH:12][C:7]([CH3:17])=[CH:8][CH:9]=1)([O-:16])(=[O:15])=[O:14].[NH4+:22]

Participants

4

Reactant 1

HCID 222Ammonia

Product 2

HCID 14594132Thietan-3-amineHCID 15911366Benzenesulfonic acid, 4-methyl-, ammonium salt (1:1)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An autoclave was charged with 3-pyridinium-thietane p-toluenesulfonate (1 g) and ammonia in methanol (7M, 20 ml). The apparatus was closed and placed in a pre-heated oil bath at 180° C. for 30 min (pressure 15 bar). The reaction mixture was cooled to room temperature then in ice bath. The yellow solution was concentrated under reduced pressure to afford the title product alongside ammonium tosylate (800 mg, NMR ratio 1:2 thietanamine:ammonium tosylate). 1H-NMR (400 MHz, DMSO-d6): 3.18 (dt, 2H), 3.36 (br s, 2H), 3.41 (dt, 2H), 4.50 (quint., 1H).

Workup

  1. customThe apparatus was closed
  2. concentrationThe yellow solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aae59a7eb9f64816b7f3ba06f3384cbf
Source dataset
uspto-grants-2015_04
Patent number
US09006456B2

Reaction notes

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