Hydrochloric Acid → cis 4-Thiocyanatomethyl-3-amino-2-oxo-azetidine hydrochloride

HRID 345650Notes

Reaction equation

HRID 345650 reaction equation
[S:1]([CH2:4][C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[N:10]1C(=O)C2=CC=CC=C2C1=O)[C:2]#[N:3].O.NN.[ClH:24]>O1CCOCC1>[ClH:24].[S:1]([CH2:4][C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH2:10])[C:2]#[N:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 86743759cis 4-Thiocyanatomethyl-3-phthalimido-2-oxo-azetidine

Product 1

HCID 86743760cis 4-Thiocyanatomethyl-3-amino-2-oxo-azetidine hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

A hot mixture of 1.45 g of the product of Step B in 15 ml of hot dioxane was cooled and 0.3 ml of hydrazine hydrate was added thereto. The mixture was stirred for 50 minutes at 20° C. and 7.5 ml of N hydrochloric acid were added thereto. The mixture was stirred for 15 hours and vacuum filtered. The filtrate was rinsed with water and the filtrate was evaporated to dryness to obtain 0.914 g of cis 4-thiocyanatomethyl-3-amino-2-oxo-azetidine hydrochloride.

Workup

  1. temperaturewas cooled
  2. stirringThe mixture was stirred for 15 hours
  3. filtrationvacuum filtered
  4. washThe filtrate was rinsed with water
  5. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-22e4e9a0a5f4461485fc82d39aa8cd50
Source dataset
uspto-grants-1991_10
Patent number
US05057512

Reaction notes

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