Phthalic Anhydride → Ditalimfos

HRID 1395627Notes

Reaction equation

HRID 1395627 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[P:12](=[S:20])([NH2:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15].C(N(CC)CC)C>O>[C:4]1(=[O:6])[N:19]([P:12](=[S:20])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:1](=[O:11])[C:2]2=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]12

Participants

5

Reactant 3

HCID 6811Phthalic AnhydrideHCID 8471TriethylamineHCID 87049Phosphoramidothioic acid, O,O-diethyl ester

Product 1

HCID 21207Ditalimfos

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
67 °C

Procedure

A mixture of 222 g (1.5 moles) phthalic anhydride, 84.5 g (0.5 moles) O,O-diethyl phosphoramidothioate and 151 g (1.5 moles) triethylamine in 800 mls light petroleum (bP 60°-80° C.) was stirred and heated at 67° C. for 5.75 hours. Two hundred and eighty mls of water were added to the vigourously stirred system. After several minutes the mixture was allowed to stand and the hot organic layer was separated and cooled to 0°-5° C. to give the desired compound, O,O-diethyl phthalimidophosphonothioate, as a colorless solid, m.p. 75°-81° C. (97.5 purity by GLC). The yield was calculated to be 55% from the O,O-diethyl phosphoramidothioate. A further 4% yield of the desired compound was obtained by filtering the cooled aqueous layer.

Workup

  1. waitAfter several minutes the mixture was allowed
  2. customthe hot organic layer was separated
  3. temperaturecooled to 0°-5° C.

Sources & evidence

ORD record
ord-d513e01dc6444378ad7b6f2f0ac4668c
Source dataset
uspto-grants-1980_05
Patent number
US04204996

Reaction notes

Loading…