Phosphoric Acid → HCID 10487654, compound

HRID 1737306Notes

Reaction equation

HRID 1737306 reaction equation
OP(O)(O)=O.[N:6]([C:9]([CH3:17])([CH3:16])[CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)=[C:7]=[O:8]>ClCCCl>[CH3:16][C:9]1([CH3:17])[NH:6][C:7](=[O:8])[C:15]2[CH:14]=[CH:13][S:12][C:11]=2[CH2:10]1

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 10797485HCID 10797485, compound

Product 1

HCID 10487654HCID 10487654, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a mixture of dry DCE (60 mL) and anhydrous H3PO4 (35 mL, prepared from 85% H3PO4 and P2O5) is added a solution of isocyanate 46 (5.12 g, 28.3 mmol) in DCE (20 mL). The resulting mixture is stirred vigorously at rt for 2 h, then at reflux for 4 h. The reaction mixture is allowed to cool and separate into two layers. The upper, organic layer is decanted, diluted with EtOAc and Na2Co3 solution, and extracted with EtOAc (2×). The organic extract is washed with brine (2×) and dried (MgSO4), filtered, and evaporated. The residue is purified by FC (6:4 CH2Cl2 /CH3CN) to give a yellow solid, mp 153-154° C. Yield: 2.10 g (41%) . 1H NMR (CDCl3) 7.43 (d, 1, J=5.2), 7.10 (d, 1, J=5.2), 6.82 (s, 1), 2.99 (s, 2), 1.38 (s, 6); 13C NMR (CDCl3) 162.64, 144.99, 130.86, 125.70, 122.96, 54.00, 37.31, 29.05; MS (EI, eE=70 eV) m/z 181 (M+), 166, 151, 148, 125, 124 (base peak), 96, 83, 70, 45; Anal. Calcd for C9H11NOS (MW=181.3): C, 59.64 H, 6.12 N, 7.73. Found: C, 59.76 H, 6.17 N, 7.87.

Workup

  1. temperatureat reflux for 4 h
  2. temperatureto cool
  3. customseparate into two layers
  4. customThe upper, organic layer is decanted
  5. additiondiluted with EtOAc and Na2Co3 solution
  6. extractionextracted with EtOAc (2×)
  7. extractionThe organic extract
  8. washis washed with brine (2×)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated
  12. customThe residue is purified by FC (6:4 CH2Cl2 /CH3CN)
  13. customto give a yellow solid, mp 153-154° C

Sources & evidence

ORD record
ord-4fdcfed247a14d19bf8c1025ca751f92
Source dataset
uspto-grants-1999_10
Patent number
US05962469

Reaction notes

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