Glycol monoethyl ether → HCID 20202807, compound

HRID 978409Notes

Reaction equation

HRID 978409 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-2d0828d1e18d492ca6eb2b6c8769dc57
Source dataset
uspto-grants-1987_05
Patent number
US04665073

Reaction notes

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