2-Ethoxy-4-(methylsulfanyl)benzoic acid → HCID 70550971, compound

HRID 1155073Notes

Reaction equation

HRID 1155073 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([S:13][CH3:14])[CH:10]=[CH:9][C:5]=1[C:6](O)=O)[CH3:2].[ClH:15].[NH2:16][C:17]1[C:22]([NH2:23])=[CH:21][N:20]=[CH:19][N:18]=1>P(Cl)(Cl)(Cl)=O>[ClH:15].[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([S:13][CH3:14])[CH:10]=[CH:9][C:5]=1[C:6]1[NH:23][C:22]2[C:17](=[N:18][CH:19]=[N:20][CH:21]=2)[N:16]=1)[CH3:2]

Participants

4

Reactant 2

HCID 134507722-Ethoxy-4-(methylsulfanyl)benzoic acidHCID 20562705Pyrimidine-4,5-diamine--hydrogen chloride (1/1)

Product 1

HCID 70550971HCID 70550971, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Three grams of 2-ethoxy-4-methylmercapto-benzoic acid and 2.2 g of 4,5-diamino-pyrimidine hydrochloride were refluxed in 30 ml of phosphorus oxychloride for three hours. The reaction mixture was poured on ice and then made ammoniacal, and the supernatant solution was decanted from the semicrystalline residue. After dissolution in methanol and filtering off from the insoluble products, the residue was purified over a silicagel column (eluate: methylene chloride/ethanol in volume ratio of from 100:0 to 98:2). The hydrochloride was precipitated from acetone with ethereal hydrochloric acid.

Workup

  1. additionThe reaction mixture was poured on ice
  2. customthe supernatant solution was decanted from the semicrystalline residue
  3. dissolutionAfter dissolution in methanol
  4. filtrationfiltering off from the insoluble products
  5. customthe residue was purified over a silicagel column (eluate: methylene chloride/ethanol in volume ratio of from 100:0 to 98:2)
  6. customThe hydrochloride was precipitated from acetone with ethereal hydrochloric acid

Sources & evidence

ORD record
ord-677e99680853497dae45200aa192ba99
Source dataset
uspto-grants-1981_11
Patent number
US04299834

Reaction notes

Loading…