Hydrochloric Acid → HCID 12788624, compound

HRID 1395598Notes

Reaction equation

HRID 1395598 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:11]([NH:13][C:14](/[C:16]/1=[CH:17]\[CH2:18][C:19](=[O:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:15])=[O:12])([OH:3])=[O:2].C(=O)(O)[O-].[Na+].[BH4-].[Na+].Cl>O>[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:11]([NH:13][C:14](/[C:16]/1=[CH:17]\[CH2:18][CH:19]([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:15])=[O:12])([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 12788623HCID 12788623, compound

Product 1

HCID 12788624HCID 12788624, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of 1-(6-carboxyhexyl)-5-((E)-3-oxooctylidene)hydantoin (20 mg.) in H2O (1.5 ml.) containing a slight excess of sodium bicarbonate was treated with sodium borohydride (5 mg.). After 60 min., the solution was acidified to Congo Red with N aqueous hydrochloric acid, the liberated carboxylic acid was extracted into ethyl acetate, and the ethyl acetate solution was thrice washed with water and dried (MgSO4). Evaporation of the ethyl acetate left a pale yellow gum (14 mg.) which was identified by 'H n.m.r. spectroscopy (characteristic signal at δ5.61 (1H, triplet =CH--, J 7.1 Hz) in deuterochloroform as 1-(6-carboxyhexyl)-5-((E)-3-hydroxyoctylidene)hydantoin.

Workup

  1. extractionthe liberated carboxylic acid was extracted into ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. customEvaporation of the ethyl acetate
  5. waitleft a pale yellow gum (14 mg.) which

Sources & evidence

ORD record
ord-ba98815e36504450b07887cd304867b3
Source dataset
uspto-grants-1980_05
Patent number
US04204068

Reaction notes

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