Cyclohexyl isocyanate → HCID 13216666, compound

HRID 434843Notes

Reaction equation

HRID 434843 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([CH:8]2[O:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])[CH:7]=1.[CH:17]1([N:23]=[C:24]=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(N(CC)CC)C.ClCCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([CH:8]2[O:12][C:11](=[O:13])[N:10]([C:24](=[O:25])[NH:23][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[C:9]2=[O:14])[CH:7]=1

Participants

5

Reactant 2

HCID 18502Cyclohexyl isocyanateHCID 13092002HCID 13092002, compound

Product 1

HCID 13216666HCID 13216666, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

5-(5-Chloro-2-methoxyphenyl)oxazolidine-2,4-dione (1.21 g., 5 mmoles) was suspended in 50 ml. of 1,2-dichloroethane. Triethylamine (1 drop) and then cyclohexylisocyanate (626 mg., 5 mmoles) were added. The reaction mixture was stirred for 19 hours at room temperature, washed in sequence with two portions of 1 N sodium hydroxide, two portions of 1 N hydrochloric acid and once with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to solids. Recrystallization from toluene gave purified 5-(5-chloro-2-methoxyphenyl)-3-cyclohexylcarbamoyloxazolidine-2,4-dione [435 mg., m.p. 150°-153° C., ir (KBr) 1818, 1761, 1527, 1493, 1364 cm-1 ].

Workup

  1. washwashed in sequence with two portions of 1 N sodium hydroxide, two portions of 1 N hydrochloric acid and once with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to solids
  5. customRecrystallization from toluene
  6. customgave
  7. custompurified 5-(5-chloro-2-methoxyphenyl)-3-cyclohexylcarbamoyloxazolidine-2,4-dione [435 mg., m.p. 150°-153° C., ir (KBr) 1818, 1761, 1527, 1493, 1364 cm-1 ]

Sources & evidence

ORD record
ord-6c6ef7c250154c36ad36cac8ed0a8507
Source dataset
uspto-grants-1983_08
Patent number
US04399296

Reaction notes

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