Hydrochloric Acid → HCID 54353160, compound

HRID 543346Notes

Reaction equation

HRID 543346 reaction equation
[O:1]=[C:2](Cl)OC(Cl)(Cl)Cl.Cl.[CH3:10][O:11][C:12](=[O:24])[CH:13]([N:21]=[N+]=[N-])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)(=O)C.C(OC)(=O)C.[Re]([O-])(=O)(=O)=O.[Na+]>[CH3:10][O:11][C:12](=[O:24])[C:13]([N:21]=[C:2]=[O:1])=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 10426DiphosgeneHCID 12170844HCID 12170844, compound

Product 1

HCID 54353160HCID 54353160, compound

Reagents, catalysts & solvents 3

HCID 5107658Sodium perrhenateCatalystHCID 6584Methyl AcetateSolventHCID 8857Ethyl AcetateSolvent

Procedure

27.3 mg (0.1 mmole) of sodium perrhenate and 1.04 grams (5.25 mmoles) of diphosgene were present at 80° C. in 1 ml of ethyl acetate saturated with hydrogen chloride. Then there were added within 20 minutes with vigorous stirring 2.05 grams (10 mmoles) of 2-azido-3-phenylpropionic acid methyl ester dissolved in 5 ml of methyl acetate. After reaction for 1 hour at 80° C., the mixture was worked up analogous to Example 1. The crude produce was distilled in a high vacuum (0.0013 mbar) at 90° to 110° C. apparatus temperature in a bulbed tube. There resulted 1.08 grams (53.2% of theory) of analytically pure 2-isocyanato-3-phenylpropenoic acid methyl ester.

Workup

  1. additionThen there were added within 20 minutes
  2. customAfter reaction for 1 hour at 80° C.
  3. customThe crude produce
  4. distillationwas distilled in a high vacuum (0.0013 mbar) at 90° to 110° C. apparatus temperature in a bulbed tube

Sources & evidence

ORD record
ord-88e180f932f24c0bad36a101ab5ace0b
Source dataset
uspto-grants-1987_04
Patent number
US04661626

Reaction notes

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