Hydrochloric Acid → (S)-4-{4-[2-(3-cyanopropylidene)hydrazino]benzyl}-1,3-oxazolidin-2-one

HRID 128987Notes

Reaction equation

HRID 128987 reaction equation
Cl.Cl.[NH:3]([C:5]1[CH:17]=[CH:16][C:8]([CH2:9][C@H:10]2[CH2:14][O:13][C:12](=[O:15])[NH:11]2)=[CH:7][CH:6]=1)[NH2:4].C(O[CH:21](OCC)[CH2:22][CH2:23][C:24]#[N:25])C>O>[C:24]([CH2:23][CH2:22][CH:21]=[N:4][NH:3][C:5]1[CH:17]=[CH:16][C:8]([CH2:9][C@H:10]2[CH2:14][O:13][C:12](=[O:15])[NH:11]2)=[CH:7][CH:6]=1)#[N:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 876164,4-DiethoxybutanenitrileHCID 45356867(S)-4-(4-Hydrazinylbenzyl)oxazolidin-2-one hydrochloride

Product 1

HCID 70196055(S)-4-{4-[2-(3-cyanopropylidene)hydrazino]benzyl}-1,3-oxazolidin-2-oneYield 93.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1M aqu. HCl (4.0 ml) was added to a solution of the product from step (a) (2.4 g) in water (35 ml). 3-Cyanopropanal diethylacetal (Aldrich, 1.7 g) was added at room temperature and the mixture stirred for 2 hours. Further acetal (0.20 g) was added and the mixture stirred for another 20 minutes. The aqueous phase was decanted from the resulting gum and extracted with ethyl acetate. The extracts were combined with the gum and evaporated in vacuo to give the desired product (2.5 g).

Workup

  1. stirringthe mixture stirred for another 20 minutes
  2. customThe aqueous phase was decanted from the resulting gum
  3. extractionextracted with ethyl acetate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-5eb1667582f14e4e906ee78fa1c028b2
Source dataset
uspto-grants-1995_11
Patent number
US05466699

Reaction notes

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