Methyl Isocyanate → HCID 13093539, compound

HRID 647191Notes

Reaction equation

HRID 647191 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]1[O:14][C:13](=[O:15])[NH:12][C:11]1=[O:16].[CH3:17][N:18]=[C:19]=[O:20]>C(N(CC)CC)C.ClCCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH:10]1[O:14][C:13](=[O:15])[N:12]([C:19](=[O:20])[NH:18][CH3:17])[C:11]1=[O:16]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 130920155-(2-Chloro-6-methoxyphenyl)-1,3-oxazolidine-2,4-dione

Product 1

HCID 13093539HCID 13093539, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

5-(2-Chloro-6-methoxyphenyl)oxazolidin-2,4-dione (1.21 g., 5 mmoles) was suspended in 25 ml. of 1,2-dichloroethane. Triethylamine (1 drop) and then methyl isocyanate (285 mg., 0.29 ml., 5 mmoles) were added and the mixture stirred for 3 hours at room temperature, by which time solution had resulted. The reaction mixture was diluted with 50 ml. of 1,2-dichloroethane, washed with two portions of saturated sodium bicarbonate and then with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to product. Recrystallization from chloroform-hexane afforded purified 5-(2-chloro-6-methoxyphenyl)-3-methylcarbamoyloxazolidin-2,4-dione [1.04 g., 70%; m.p. 124°-127° C. (dec); m/e 300/298].

Workup

  1. customhad resulted
  2. additionThe reaction mixture was diluted with 50 ml
  3. washof 1,2-dichloroethane, washed with two portions of saturated sodium bicarbonate
  4. dry with materialwith brine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to product
  7. customRecrystallization from chloroform-hexane
  8. customafforded
  9. custompurified 5-(2-chloro-6-methoxyphenyl)-3-methylcarbamoyloxazolidin-2,4-dione [1.04 g., 70%; m.p. 124°-127° C. (dec); m/e 300/298]

Sources & evidence

ORD record
ord-e7b0d93f20bc42fb91c3a3227ae9735a
Source dataset
uspto-grants-1983_10
Patent number
US04407811

Reaction notes

Loading…