Water → Diethyl 4-isothiocyanatobenzylphosphonate

HRID 25512Notes

Reaction equation

HRID 25512 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[CH:20]=[CH:19][C:9]([CH2:10][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+].O>ClCCl>[N:5]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][P:11](=[O:18])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17])=[CH:19][CH:20]=1)=[C:1]=[S:2]

Participants

6

Reactant 4

HCID 962WaterHCID 10040ThiophosgeneHCID 88358Diethyl p-aminobenzylphosphonateHCID 516892Sodium Bicarbonate

Product 1

HCID 22568434Diethyl 4-isothiocyanatobenzylphosphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thiophosgene (4.1 mL, 54 mmol) was added al at once to a mixture of diethyl 4-aminobenzylphosphonate (12.04 g, 50 mmol), sodium bicarbonate (8.33 g, 99 mmol), water (100 mL), and dichloromethane (250 mL), and the mixture was stirred at room temperature for about 2 hours. The organic and aqueous layers were separated, the organic layer dried over magnesium sulfate, filtered, and concentrated to give the product isothiocyanate as a brown oil. This was used directly in the next step.

Workup

  1. customThe organic and aqueous layers were separated
  2. dry with materialthe organic layer dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2c8f5600ae6f41b9984d67f20d309d62
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Reaction notes

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