Sodium Hydroxide → HCID 178428945, compound

HRID 246849Notes

Reaction equation

HRID 246849 reaction equation
[OH-].[Na+].C(=O)(O)O.[NH2:7][C:8]([NH2:10])=[NH:9].[O-]S([O-])(=O)=O.[Na+].[Na+].[CH2:18]([O:25][C:26]1[CH:31]=[C:30]([CH3:32])[C:29]([N:33]=[C:34]=[O:35])=[C:28]([CH3:36])[CH:27]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[ClH:37].CO>C1COCC1.CO>[ClH:37].[CH2:18]([O:25][C:26]1[CH:27]=[C:28]([CH3:36])[C:29]([NH:33][C:34]([NH:9][C:8](=[NH:10])[NH2:7])=[O:35])=[C:30]([CH3:32])[CH:31]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 5

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 286947Carbonic acid-guanidine (1:1)HCID 13369958HCID 13369958, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 178428945HCID 178428945, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 50% NaOH aqueous solution (8.0 g) is added to a suspension of guanidine carbonate (9.0 g) in 200 ml of THF. The mixture is stirred for one hour, after which 15.0 grams of anhydrous Na2SO4 are added and the mixture stirred an additional hour. A solution of 4-benzyloxy-2,6-dimethylphenyl isocyanate (12.7 g) in 100 ml HTF is added to the mixture over a period of 4 hours. The reaction mixture is allowed to stand overnight, filtered, and the filtrate concentrated under vacuum. The filtrate is partitioned between H2O and CHCl3. The two layers are filtered to remove insoluble materials and then separated. The aqueous layer is extracted with CHCl3 and the combined CHCl3 extracts dried and concentrated under vacuo to give a tan solid. This solid is dissolved in methanol and acidified with HCl/methanol. Methanol is removed under vacuo to give a solid which is crystallized from methanol/acetonitrile to give after filtering and vacuum drying 9.8 grams of the desired amidinourea hydrochloride, M.P. 181°-183° C.

Workup

  1. stirringthe mixture stirred an additional hour
  2. waitto stand overnight
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe filtrate is partitioned between H2O and CHCl3
  6. filtrationThe two layers are filtered
  7. customto remove insoluble materials
  8. customseparated
  9. extractionThe aqueous layer is extracted with CHCl3
  10. dry with materialthe combined CHCl3 extracts dried
  11. concentrationconcentrated under vacuo
  12. customto give a tan solid
  13. customMethanol is removed under vacuo
  14. customto give a solid which
  15. customis crystallized from methanol/acetonitrile
  16. customto give
  17. filtrationafter filtering
  18. dry with materialvacuum drying 9.8 grams of the desired amidinourea hydrochloride, M.P. 181°-183° C.

Sources & evidence

ORD record
ord-81d027e2c07842a7838dc1f920bc98a2
Source dataset
uspto-grants-1987_11
Patent number
US04704401

Reaction notes

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