Dichloromethane → HCID 20535125, compound

HRID 1156605Notes

Reaction equation

HRID 1156605 reaction equation
[NH2:1][C:2]1[N+:7]([O-:8])=[C:6]([NH2:9])[N:5]=[C:4]([N:10]([CH2:14][CH:15]=[CH2:16])[CH2:11][CH:12]=[CH2:13])[N:3]=1.C(Cl)Cl.[C:20](Cl)(Cl)=[O:21].[OH-].[Na+]>C1(C)C=CC=CC=1.CO>[NH2:9][C:6]1[N:7]2[O:8][C:20](=[O:21])[N:1]=[C:2]2[N:3]=[C:4]([N:10]([CH2:14][CH:15]=[CH2:16])[CH2:11][CH:12]=[CH2:13])[N:5]=1

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 178457172HCID 178457172, compound

Product 1

HCID 20535125HCID 20535125, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

75 g. of 2,4-diamino-6-diallylamino-s-triazine-3-oxide are suspended in 800 ml. of methylene chloride and cooled while stirring to 0° C. At this temperature there are then simultaneously added dropwise within 45 minutes 180 ml. of 20% phosgene in toluene and sufficient 10% sodium hydroxide to hold the pH at 7-7.5. The mixture is subsequently stirred for a further 1 hour. Methylene chloride and methanol are then added in order to dissolve the precipitated product. The two phases are separated and the aqueous phase is extracted twice with methylene chloride. The combined organic extracts are dried over magnesium sulfate and evaporated under reduced pressure, there being obtained 7-amino-5-diallylamino-2H-[1,2,4]oxadiazolo[2,3-a]-s-triazin-2-one, having a melting point of 211°-213° C.

Workup

  1. additionAt this temperature there are then simultaneously added dropwise within 45 minutes 180 ml
  2. stirringThe mixture is subsequently stirred for a further 1 hour
  3. dissolutionto dissolve the precipitated product
  4. customThe two phases are separated
  5. extractionthe aqueous phase is extracted twice with methylene chloride
  6. dry with materialThe combined organic extracts are dried over magnesium sulfate
  7. customevaporated under reduced pressure, there

Sources & evidence

ORD record
ord-b7e84c0a03984d6eb01b724d0e87a3ca
Source dataset
uspto-grants-1982_06
Patent number
US04336380

Reaction notes

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