Carbon Dioxide → HCID 86746568, compound

HRID 2082590Notes

Reaction equation

HRID 2082590 reaction equation
[C:1](=[O:3])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:15]([O:22][C:23](=[O:26])[CH2:24][NH2:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>ClCCl.C(OCC)C>[N-:25]=[C:1]=[O:3].[CH2:15]([O:22][C:23](=[O:26])[CH2:24][NH2:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 280Carbon Dioxide2×HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 6451311O-benzylglycine toluene-p-sulphonate

Product 1

HCID 86746568HCID 86746568, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Carbon dioxide was added subsurface to a dichloromethane (20 mL) solution containing glycine benzyl ester p-toluenesulfonic acid salt (0.01 mol, 3.37 g) and triethylamine (0.04 mol, 4.0 g) at -10° C. (ice and salt bath) for 30 min at a pressure of 0 psig. The reaction mixture was transferred via cannula all at once under carbon dioxide to the precooled solution of phosphorus oxychloride (0.01 mol, 1.6 g) in 20 mL dichloromethane. After stirring for 20 min at -10° C. diethylether (40 mL) was added to the reaction mixture. A white ppt formed and was filtered off. The filtrate was concentrated in vacuo and the residue was extracted with 3×20 mL diethylether. The ether layers were concentrated and the residue distilled under vacuum (ca. 0.1-0.3 torr) collecting product, glycine benzyl ester isocyanate, at 105°-106° C. (0.91 g, 47.5%) of 98% purity as judged by GC. IR (neat) 2253, 1747 cm-1. 1H NMR (CDCl3) δ 7.37 (s, 5H), 5.24 (s, 2H), 3.96 (s, 2H) ppm.

Workup

  1. additionwas added to the reaction mixture
  2. customA white ppt formed
  3. filtrationwas filtered off
  4. concentrationThe filtrate was concentrated in vacuo
  5. extractionthe residue was extracted with 3×20 mL diethylether
  6. concentrationThe ether layers were concentrated
  7. distillationthe residue distilled under vacuum (ca. 0.1-0.3 torr)
  8. customcollecting product, glycine benzyl ester isocyanate
  9. customat 105°-106° C.

Sources & evidence

ORD record
ord-8788f6adf9e3460a8f686c7a765db6a6
Source dataset
uspto-grants-1993_02
Patent number
US05189205

Reaction notes

Loading…