Guanidine → HCID 15364539, compound

HRID 501941Notes

Reaction equation

HRID 501941 reaction equation
[N+](=C)=[N-].CN(N=O)C(N[N+]([O-])=O)=N.[OH-].[Na+].N[C:17](N)=N.[C:20]([O:28][CH:29]([P:33]([O:38][CH2:39][CH3:40])([O:35][CH2:36][CH3:37])=[O:34])[C:30]([OH:32])=[O:31])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>ClCCl.C(OCC)C>[C:20]([O:28][CH:29]([P:33]([O:35][CH2:36][CH3:37])([O:38][CH2:39][CH3:40])=[O:34])[C:30]([O:32][CH3:17])=[O:31])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 5

HCID 3520GuanidineHCID 9550DiazomethaneHCID 14798Sodium HydroxideHCID 15364541HCID 15364541, compoundHCID 135436526N-Methyl-N'-nitro-N-nitrosoguanidine

Product 1

HCID 15364539HCID 15364539, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Diazomethane was generated in 3 fire-polished erlenmeyer flasks using ⅓ of each N-methyl-N′-nitro-N-nitrosoguanidine (17.1 g 116. mmol), 5 M sodium hydroxide (200 mL), and diethyl ether (450 mL) at 0° C. by adding the guanidine in small portions with swirling to the other two. After addition was complete, the mixture was allowed to stand at 0° C. for 10 min with occasional swirling. The ethereal was transferred in portions to a suspension of 2-(benzoyloxy)-2-(diethoxyphosphoryl)acetic acid (21.0 g, 66.4 mmol) in dichloromethane (ca. 20 mL) until the solid had all dissolved and a yellow color persisted. The reaction was allowed to rest at 0° C. for 15 min, before bubbling nitrogen through the solution to remove most of the unreacted diazomethane (reaction went almost colorless). The reaction was concentrated to give the 22.0 g (quant.) as a faint yellow oil which was used without purification. 1H-NMR (CDCl3, 500 MHz) δ 1.37 (m, 6H), 3.85 (s, 3H), 4.28 (m, 4H), 5.71 (d, J=16.8, 1H), 7.47 (m, 2H), 7.61 (m, 1H), 8.11 (m, 2H).

Workup

  1. customat 0° C.
  2. additionAfter addition
  3. dissolutionall dissolved
  4. waitto rest at 0° C. for 15 min
  5. custombefore bubbling nitrogen through the solution
  6. customto remove most of the unreacted diazomethane (
  7. customreaction
  8. concentrationThe reaction was concentrated
  9. customto give the 22.0 g (quant.) as a faint yellow oil which
  10. customwas used without purification

Sources & evidence

ORD record
ord-f71ab8eeb52b4bafa6d8895c0e4185f0
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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