Glycol monoethyl ether → HCID 20202807, compound

HRID 543791Notes

Reaction equation

HRID 543791 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[H-].[Na+].C(OCCO)C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19](Br)[N:18]=1>>[NH2:16][C:17]1[N:18]=[C:19]([S:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 24758Sodium hydrideHCID 257004-Mercaptobutanoic acidHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 20202807HCID 20202807, compoundYield 62.9%

Procedure

A mixture of 4-mercaptobutyric acid (0.72 g.) a 50% w/w dispersion of sodium hydride in mineral oil (0.58 g.) and 2-ethoxyethanol (5 ml.) was treated with 2-amino-6-bromopyridine (0.35 g.) and the mixture was heated under reflux for 18 hours and then evaporated to dryness. The residue was partitioned between water and EtOAc and the aqueous phase was neutralised with HOAc. The precipitated yellow solid was collected to give 4-(6-aminopyrid-2-ylthio)butyric acid (0.27 g.) which was used without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. customevaporated to dryness
  4. customThe residue was partitioned between water and EtOAc
  5. customThe precipitated yellow solid was collected

Sources & evidence

ORD record
ord-c4976b5d05b74660887d802a1713b976
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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