Ethyl isocyanate → HCID 178465288, compound

HRID 1447152Notes

Reaction equation

HRID 1447152 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([C:15]([OH:17])=[O:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH2:18]([N:20]=[C:21]=[O:22])[CH3:19].C(N(CC)CC)C>CN(C)C=O>[CH2:18]([NH:20][C:21]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([C:15]([OH:17])=[O:16])=[CH:10][N:9]=2)=[CH:6][CH:7]=1)=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanate2×HCID 8471TriethylamineHCID 178507442HCID 178507442, compound

Product 1

HCID 178465288HCID 178465288, compoundYield 24.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4.6 g (20 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid, 2.36 ml (30 mmol) of ethyl isocyanate, and 70 ml of dimethylformamide is stirred at room temperature and 2.8 ml (20 mmol) of triethylamine is added. The resulting solution is allowed to stand overnight at room temperature and another 2.36 ml (20 mmol) of ethyl isocyanate is added. After 6 hrs the dimethylformamide is evaporated under high vacuum and the residue is treated with 100 ml of water. The solid is filtered and dried to give 1.5 g of 2-[4-(N-ethylcarbamoylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid. The filtrate is acidified to pH 2.5 with hydrochloric acid and another 3.10 g of acid is obtained.

Workup

  1. customAfter 6 hrs the dimethylformamide is evaporated under high vacuum
  2. additionthe residue is treated with 100 ml of water
  3. filtrationThe solid is filtered
  4. customdried

Sources & evidence

ORD record
ord-0bda0ef7b1f546c3a73a25e61e82bba0
Source dataset
uspto-grants-1982_02
Patent number
US04315933

Reaction notes

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