Triethyl phosphite → [phosphono(thiomorpholin-4-yl)methyl]phosphonic acid

HRID 1608124Notes

Reaction equation

HRID 1608124 reaction equation
C(Cl)(=O)C(Cl)=O.[CH:7]([N:9]1[CH2:14][CH2:13][S:12][CH2:11][CH2:10]1)=O.[P:15]([O:22]CC)([O:19]CC)[O:16]CC>C(Cl)Cl>[N:9]1([CH:7]([P:15](=[O:16])([OH:22])[OH:19])[P:15](=[O:22])([OH:19])[OH:16])[CH2:14][CH2:13][S:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 31215Triethyl phosphite2×HCID 65578Oxalyl chlorideHCID 18926902Thiomorpholine-4-carbaldehyde

Product 1

HCID 406062[phosphono(thiomorpholin-4-yl)methyl]phosphonic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (16.6 ml) was added dropwise at 0° C. to a stirred solution of N-formyl-thiomorpholine (26.2 g) in methylene chloride (200 ml). The mixture was stirred at room temperature until the gas evolution ceased (about 5 hours later). Triethyl phosphite (66 ml) was then added during 1.5 hours at room temperature. Unreacted triethyl phosphite was removed in vacuo, and the residue was refluxed with 20% hydrochloric acid (150 ml) for 3 hours. The mixture was evaporated to dryness in vacuo, and the residue was stirred with acetone. The crystalline product was filtered and recrystallized from water. M.p.: >250° C. (dec.).

Workup

  1. customabout 5 hours
  2. customwas removed in vacuo
  3. temperaturethe residue was refluxed with 20% hydrochloric acid (150 ml) for 3 hours
  4. customThe mixture was evaporated to dryness in vacuo
  5. stirringthe residue was stirred with acetone
  6. filtrationThe crystalline product was filtered
  7. customrecrystallized from water

Sources & evidence

ORD record
ord-8fa164d3425947b2a68c81738aafb8f8
Source dataset
uspto-grants-1989_09
Patent number
US04870063

Reaction notes

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