Hydrochloric Acid → HCID 541553, compound

HRID 1679425Notes

Reaction equation

HRID 1679425 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH:6]([N:9]=[C:10]=[O:11])([CH3:8])[CH3:7].O.Cl>[OH-].[Na+].CC(C)=O>[CH:6]([NH:9][C:10](=[O:11])[NH:1][CH2:2][C:3]([OH:5])=[O:4])([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 962WaterHCID 61277Isopropyl isocyanate

Product 1

HCID 541553HCID 541553, compoundYield 48.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of glycine (75.1 g.) in normal sodium hydroxide solution (one litre) is heated at 36° C. A solution of isopropyl isocyanate (76.5 g.) in acetone (100 cc.) is then added dropwise, whilst stirring. A rise in temperature from 36° to 50° C is observed in the course of the addition. The reaction mixture is stirred for a further 30 minutes after the end of the addition. Crushed ice (500 g.) and water (250 cc.) are then added and the mixture is acidified by adding 5 N hydrochloric acid (200 cc.), while stirring. The precipitate is then filtered off, and dried. 2-(3-Isopropylureido)-acetic acid (70 g.) melting at 178° C is thus obtained. A second crop (44 g.) of 2-(3-isopropylureido)-acetic acid, melting at 178° C, is obtained by concentrating the filtrate.

Workup

  1. additionA rise in temperature from 36° to 50° C is observed in the course of the addition
  2. stirringThe reaction mixture is stirred for a further 30 minutes
  3. additionafter the end of the addition
  4. stirringwhile stirring
  5. filtrationThe precipitate is then filtered off
  6. customdried

Sources & evidence

ORD record
ord-00a053c14cdf428d8cad73c1f902c6d6
Source dataset
uspto-grants-1978_03
Patent number
US04080473

Reaction notes

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