Hydrochloric Acid → Diisopropyl Ether

HRID 1282019

Reaction equation

HRID 1282019 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[Cl:13][CH2:14][CH2:15][O:16][C:17](Cl)=[O:18].O.O.O.O.O.O.O.O.O.O.O.O.P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+].Cl.Cl[CH2:42]Cl>>[Cl:13][CH2:14][CH2:15][O:16][C:17]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1)=[O:18].[CH:15]([O:16][CH:8]([CH3:9])[CH3:12])([CH3:42])[CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 123052-Chloroethyl chloroformateHCID 430264-Aminohydratropic acidHCID 61473Trisodium phosphate dodecahydrate

Product 2

HCID 7914Diisopropyl EtherHCID 184235752-(4-{[(2-Chloroethoxy)carbonyl]amino}phenyl)propanoic Acid

Procedure

1 g (6 mmol) of 2-(4-aminophenyl)propanoic acid was suspended in 30 ml of dichloromethane and 1.24 ml (12 mmol) of 2-chloroethylchloroformate were added at 0° C. under stirring. After 30 minutes at the same temperature 2.27 g (6 mmol) of sodium phosphate dodecahydrate were added portionwise. After 4 hours the reaction was complete (HPLC-MS). The mixture was made acidic by using hydrochloric acid 0.5N and the product extracted with dichloromethane. The organic layer was dried over sodium sulphate and evaporated under vacuum. 1.4 g (100%yield) of the title compound were obtained by crystallization from diisopropylether.

Workup

  1. extractionthe product extracted with dichloromethane
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated under vacuum

Sources & evidence

ORD record
ord-b8fe52451ece4672826b8d63fb756574
Source dataset
uspto-grants-2002_09
Patent number
US06455559B1

Linked notes

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