Hydrochloric Acid → HCID 13563094, compound

HRID 482690Notes

Reaction equation

HRID 482690 reaction equation
[C:1]12([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]1)[C:10]1[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:4](=[O:11])[CH2:3][CH2:2]2.CO.[BH4-].[Na+].Cl>[Cl-].[Na+].O>[OH:11][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:1]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 13563098HCID 13563098, compound

Product 1

HCID 13563094HCID 13563094, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

To a slurry of 14.3 g. (0.062 mole) of 3',4'-dihydrospiro[imidazolidine-4,1'(2'H)-naphthalene]2,4',5-trione in 250 ml. of methanol at 0° C. was added in small portions over a period of 15 minutes 4.8 g. (0.13 mole) of sodium borohydride, and the reaction mixture allowed to stir in the cold for 60 minutes. The reaction mixture was added to 250 ml. of 10% hydrochloric acid and 50 ml. of a brine solution. The product was extracted with ethyl acetate (5×50 ml.) and the extracts combined and washed with a 10% hydrochloric acid solution. The extracts were dried over magnesium sulfate and concentrated to give an off-white solid. Triturations with diethyl ether followed by filtration gave 4.5 g. (31.9% yield).

Workup

  1. additionThe reaction mixture was added to 250 ml
  2. extractionThe product was extracted with ethyl acetate (5×50 ml.)
  3. washwashed with a 10% hydrochloric acid solution
  4. dry with materialThe extracts were dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give an off-white solid
  7. filtrationTriturations with diethyl ether followed by filtration
  8. customgave 4.5 g

Sources & evidence

ORD record
ord-c9be14dd0a8f49d0ae81705a245b6fba
Source dataset
uspto-grants-1986_03
Patent number
US04575507

Reaction notes

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