Formaldehyde → Tetrahydro-N-methyl-N-(phosphonomethyl)-3-thiophenamine 1,1-dioxide

HRID 2051676

Reaction equation

HRID 2051676 reaction equation
Cl.[CH3:2][NH:3][CH:4]1[CH2:8][CH2:7][S:6](=[O:10])(=[O:9])[CH2:5]1.[CH2:11]=O.[P:13]([OH:16])([OH:15])[OH:14].O>C(O)C>[CH3:2][N:3]([CH2:11][P:13]([OH:16])([OH:15])=[O:14])[CH:4]1[CH2:8][CH2:7][S:6](=[O:10])(=[O:9])[CH2:5]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 107909Phosphorous acidHCID 27708173-(Methylamino)-1lambda6-thiolane-1,1-dione hydrochloride

Product 1

HCID 20509047Tetrahydro-N-methyl-N-(phosphonomethyl)-3-thiophenamine 1,1-dioxideYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-methyltetrahydro-3-thiophenamine 1,1-dioxide hydrochloride (37.2 parts, 0.20 mole); 90 percent paraformaldehyde (6.8 parts, 0.22 mole); orthophosphorous acid (18.0 parts, 0.22 mole); and water (30 parts) was heated at its reflex temperature for 3 hours. After cooling, the solution was stirred into ethanol (150 ml.) and the sticky, white precipitate was triturated under more ethanol. After being dried in vacuo over P2O5 the product weighed 42.0 g. (86.3 percent yield). m.p. 222°-225° C.

Workup

  1. temperatureAfter cooling
  2. customthe sticky, white precipitate was triturated under more ethanol
  3. dry with materialAfter being dried in vacuo over P2O5 the product

Sources & evidence

ORD record
ord-5da9cf5125984a4f8fe5fd7dcf6c9322
Source dataset
uspto-grants-1980_01
Patent number
US04181806

Linked notes

Loading…