Sodium Hydroxide → HCID 21475335, compound

HRID 2294632Notes

Reaction equation

HRID 2294632 reaction equation
Cl[CH2:2][O:3][CH2:4][CH3:5].[CH3:6][S:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)=[O:10].[OH-].[Na+].P([O-])(O)(O)=O.[K+]>ClCCl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[CH2:4]([O:3][CH2:2][N:11]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=1)[C:9](=[O:10])[CH2:8][S:7][CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 18523Chloromethyl ethyl etherHCID 516951Monobasic potassium phosphateHCID 21475347HCID 21475347, compound

Product 1

HCID 21475335HCID 21475335, compoundYield 102.3%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Chloromethyl ethylether (18.1 g) was added dropwise, during 20 minutes, to a vigorously stirred mixture of crude product of Step 1 (21.8 g) dissolved in dichloromethane (50 ml), 52% aqueous sodium hydroxide (34 g) and benzyl triethylammonium chloride (0.2 g), with water-bath cooling to 20° C. After 30 minutes the mixture was treated with saturated aqueous potassium dihydrogen phosphate until pH 8, at 20° C., extracted with dichloromethane (5×100 ml), the extract dried over sodium sulphate, filtered and concentrated under reduced pressure to give the crude product as a yellow oil (27.5 g). 1H NMR (CDCl3): δ 1.23(3 H,t); 2.21(3 H,s); 3.0(2 H,s); 3.68(2 H,bq); 5.1(2H,s); 7.58(4 H,m).

Workup

  1. extractionextracted with dichloromethane (5×100 ml)
  2. dry with materialthe extract dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6248917457e24534a6466fb390c4414a
Source dataset
uspto-grants-1997_11
Patent number
US05688962

Reaction notes

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