Formamide → 3-Amino-2,2,4,4-tetramethylthietane

HRID 232337

Reaction equation

HRID 232337 reaction equation
[CH:1]([NH2:3])=O.[CH3:4][C:5]1([CH3:12])[C:8](=O)[C:7](C)([CH3:10])[S:6]1.B(O)(O)O>O>[NH2:3][CH:1]1[C:7]([CH3:10])([CH3:8])[S:6][C:5]1([CH3:12])[CH3:4]

Participants

5

Reactant 3

HCID 713FormamideHCID 7628Boric AcidHCID 2822142,2,4,4-Tetramethylthietan-3-one

Product 1

HCID 115210993-Amino-2,2,4,4-tetramethylthietaneYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

Formamide (4.0 g, 89 mmol), 2,2,4,4-tetramethyl-3-oxothietane (1.0 g, 6933 mmol) and boric acid (100 mg) were combined in a Teflon lined Parr bomb which was heated for 15 hours in a 175° C. oil bath. The reaction was cooled and the light brown mixture taken up in water (40 ml). The aqueous solution was extracted with methylene chloride (4×20 ml) and the combined extracts dried (MgSO4) and evaporated under reduced pressure to a light brown oil (1.02 g). The residue was hydrolyzed and the hydrolyzate worked up according to the procedure of Example 1 to give the title product 650 mg (65%), verified by its 1H-NMR spectrum.

Workup

  1. temperatureThe reaction was cooled
  2. extractionThe aqueous solution was extracted with methylene chloride (4×20 ml)
  3. dry with materialthe combined extracts dried (MgSO4)
  4. customevaporated under reduced pressure to a light brown oil (1.02 g)

Sources & evidence

ORD record
ord-ae832359f86a4740a2a0aded07d8bfb6
Source dataset
uspto-grants-1989_07
Patent number
US04851548

Linked notes

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