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

HRID 1389026

Reaction equation

HRID 1389026 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 reflux 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. temperaturereflux temperature for 3 hours
  2. temperatureAfter cooling
  3. customthe sticky, white precipitate was triturated under more ethanol
  4. dry with materialAfter being dried in vacuo over P2O5 the product

Sources & evidence

ORD record
ord-6d49478bb54e4cd3bd5876e289607326
Source dataset
uspto-grants-1981_01
Patent number
US04243524

Linked notes

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