Ammonia → HCID 178463890, compound

HRID 1679266Notes

Reaction equation

HRID 1679266 reaction equation
O.[C:2]([OH:14])(=[O:13])[CH2:3][C:4]([CH2:9][C:10]([OH:12])=O)(C(O)=O)O.S(=O)(=O)(O)O.S(O)(O)(=O)=O.[CH2:25]([N:27]([CH2:31][CH3:32])[C:28]([NH2:30])=[NH:29])[CH3:26].N>O>[OH:12][C:10]1[CH:9]=[C:4]([CH2:3][C:2]([OH:14])=[O:13])[N:30]=[C:28]([N:27]([CH2:31][CH3:32])[CH2:25][CH3:26])[N:29]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 223902Sulfuric acid--N,N-diethylguanidine (1/1)

Product 1

HCID 178463890HCID 178463890, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Powdered citric acid monohydrate (42.0 g) was added in small portions over one hour to concentrated sulphuric acid (180 ml) at 0° C and the mixture stirred until a clear solution was obtained. N,N-Diethylguanidine sulphate (32.8 g) was added over 15 minutes and the solution stirred for one hour at the ambient temperature (ca 22°-24° C) and then at 90° C for a further 2 hours. After dilution of the mixture with deionised water (1050 ml), ammonia solution (s.g. 0.880) was added to adjust the pH to 4, and the mixture cooled to 0° C for one hour. The precipitate was collected by filtration, washed with ice-water (20 ml), acetone (100 ml), and with ether (100 ml) to yield 4-hydroxy-2-diethylaminopyrimidin-6-yl acetic acid as a white powder, having a melting point (with decomposition) of 156°-157° C.

Workup

  1. customwas obtained
  2. stirringthe solution stirred for one hour at the ambient temperature (ca 22°-24° C)
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ice-water (20 ml), acetone (100 ml)

Sources & evidence

ORD record
ord-db942bb1d3c648a6819b2a166c3f7555
Source dataset
uspto-grants-1978_03
Patent number
US04080326

Reaction notes

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