Triethylamine → HCID 178514103, compound

HRID 2286611Notes

Reaction equation

HRID 2286611 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]([OH:18])[C:15]([C:19]([OH:21])=[O:20])=[CH:14][N:13]=2)=[CH:8][CH:7]=1)=[O:4].C(N(CC)CC)C.[O-:29][C:30]#[N:31].[K+]>O>[C:30]([NH:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:17]=[C:16]([OH:18])[C:15]([C:19]([OH:21])=[O:20])=[CH:14][N:13]=2)=[CH:10][CH:11]=1)=[O:4])(=[O:29])[NH2:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11378442Potassium cyanate2×HCID 178511432HCID 178511432, compound

Product 1

HCID 178514103HCID 178514103, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.928 g (3.2 mmol ) of 2-[4-(N-glycylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid and 25 ml of water is treated with 1 ml (7.2 mmol) of triethylamine followed by 1.3 g (16 mmol) of potassium cyanate. After standing at room temperature overnight a 0.5 g (6.2 mmol) portion of potassium cyanate is added and the reaction mixture is allowed to stand at room temperature for another 18 hrs. The solution is concentrated in vacuo to 1/3 its volume and acidified to pH 2.5 with hydrochloric acid. The product is filtered, washed with water, ethanol, and ether to give 1.0 g of 2-[4-(N-carbamoylglycylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid.

Workup

  1. waitto stand at room temperature for another 18 hrs
  2. concentrationThe solution is concentrated in vacuo to 1/3 its volume
  3. filtrationThe product is filtered
  4. washwashed with water, ethanol, and ether

Sources & evidence

ORD record
ord-56f18216397344b1af320d4f4ab22706
Source dataset
uspto-grants-1981_05
Patent number
US04267180

Reaction notes

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