Phenyl isocyanate → HCID 15049043, compound

HRID 484553Notes

Reaction equation

HRID 484553 reaction equation
[Cl-].[C:2]([CH2:5][O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[NH3+:13])([OH:4])=[O:3].[C:14]1([N:20]=[C:21]=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>[OH-].[Na+]>[C:14]1([NH:20][C:21](=[O:22])[NH:13][C@@H:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C@H:7]2[O:6][CH2:5][C:2]([OH:4])=[O:3])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 67747384HCID 67747384, compound

Product 1

HCID 15049043HCID 15049043, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of trans-2-carboxymethoxy-cyclohexyl ammonium chloride (0.419 g, 2 mmoles) in 2N NaOH (10 ml), phenylisocyanate (0.476 g, 4 mmoles) was added under stirring. After 1 hour the solution was extracted with diethyl ether (10 ml) and the aqueous phase was acidified with HCl 18% to pH 3. The title compound separated in the form of white crystals, which were filtered off and dried over P2O5. Thus, there were obtained 0.23 g (40%) of the title compound, melting point 166°-168° C.

Workup

  1. extractionAfter 1 hour the solution was extracted with diethyl ether (10 ml)
  2. customThe title compound separated in the form of white crystals, which
  3. filtrationwere filtered off
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-6aec0ad471b44907b25d4bb1fb1ed602
Source dataset
uspto-grants-1993_07
Patent number
US05231216

Reaction notes

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