Thiourea → Thiourea

HRID 1632936Notes

Reaction equation

HRID 1632936 reaction equation
[CH3:1][O:2][P:3]([O:21]C)([N:5]1[CH2:8][C@H:7]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]1=[O:20])=[O:4].[NH2:23][C:24]([NH2:26])=[S:25]>C(#N)C>[O:20]=[C:6]1[C@@H:7]([NH:9][C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:19])[CH2:8][N:5]1[P:3](=[O:4])([O-:21])[O:2][CH3:1].[C:24]([NH2:26])([NH2:23])=[S:25]

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 13366878HCID 13366878, compound

Product 2

HCID 2723790ThioureaHCID 131713939HCID 131713939, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-[1-(Dimethoxyphosphinyl)-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester (100 mg; see example 1) was dissolved in 2 ml of acetonitrile, thiourea (23 mg) was added, and the mixture was refluxed under a nitrogen atmosphere for 20 hours. Solvent was then removed in vacuo and the residue was worked into a hygroscopic powder by triturating several times with anhydrous ether yielding (S)-[2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinyl]phosphonic acid, methyl ester, thiuronium salt.

Workup

  1. temperaturethe mixture was refluxed under a nitrogen atmosphere for 20 hours
  2. customSolvent was then removed in vacuo
  3. customby triturating several times with anhydrous ether

Sources & evidence

ORD record
ord-f59fc69107494607a3203c95635475e6
Source dataset
uspto-grants-1984_10
Patent number
US04478749

Reaction notes

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