Iodoethane → HCID 53799998, compound

HRID 1975354Notes

Reaction equation

HRID 1975354 reaction equation
[SH:1][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:21](I)[CH3:22].[OH-].[Na+]>O1CCCC1.O>[CH2:21]([S:1][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1)=[O:4])[CH3:22]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 745787Benzoic acid, 4-[(mercaptoacetyl)amino]-

Product 1

HCID 53799998HCID 53799998, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

15 g of 4-mercaptoacetylaminobenzoic acid are dissolved in 450 ml of tetrahydrofuran, and 39.2 g of potash and 17.24 ml of ethyl iodide in 50 ml of tetrahydrofuran are added thereto. The mixture is stirred overnight and 200 ml of water and a small amount of 2N NaOH are added thereto. The cloudy solution is filtered, and the filtrate is acidified with concentrated HCl. The yellow crystals are filtered off with suction and recrystallised from isopropanol, yielding 4-ethylmercaptoacetylaminobenzoic acid having a melting point of 209°-211°.

Workup

  1. filtrationThe cloudy solution is filtered
  2. filtrationThe yellow crystals are filtered off with suction
  3. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-ac82c8f059ae41a4ac262b559f3f22e0
Source dataset
uspto-grants-1994_02
Patent number
US05286728

Reaction notes

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