Cyclohexyl isocyanate → HCID 13216666, compound

HRID 544315Notes

Reaction equation

HRID 544315 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 1N sodium hydroxide, two portions of 1N 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 1N sodium hydroxide, two portions of 1N 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-cc2d7534e6d24d45952ab800f783b789
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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