Ethanethiol → HCID 15239984, compound

HRID 1653640Notes

Reaction equation

HRID 1653640 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[C:5]([O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=2)=[CH:4][CH:3]=1.[CH2:22]([SH:24])[CH3:23].P(OC#N)(OCC)(OCC)=O.C(N(CC)CC)C>O.C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[S:24][CH2:22][CH3:23])[C:5]([O:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 8471TriethylamineHCID 15239982HCID 15239982, compoundHCID 18315342HCID 18315342, compound

Product 1

HCID 15239984HCID 15239984, compoundYield 34.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.5 g (8.5 mmol) of 6-amino-3-[(4,6-dimethoxypyrimidin-2-yl)oxy]picolinic acid, 0.64 g (10.3 mmol) of ethylmercaptan, 2.8 g (17 mmol) of diethyl cyano phosphate and 1.73 g (17.1 mmol) of triethylamine were added to a THF solution, and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate, followed by separation, washed with water and dried. Then, the solvent was distilled off, and the residual oily product was purified by column chromatography to obtain the desired product as colorless transparent crystals.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. customfollowed by separation
  4. washwashed with water
  5. customdried
  6. distillationThen, the solvent was distilled off
  7. customthe residual oily product was purified by column chromatography

Sources & evidence

ORD record
ord-14d9beffe3244596afb800943c123805
Source dataset
uspto-grants-1995_04
Patent number
US05403816

Reaction notes

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