N-methoxy-N-methylcarbamoyl chloride → N'-(3-chloro-4-(2-oxo-3-oxazolidinyl)phenyl)-N-methoxy-N-methylurea

HRID 903001Notes

Reaction equation

HRID 903001 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH2:11][O:10][C:9]2=[O:13])=[C:4]([Cl:14])[CH:3]=1.[CH3:15][O:16][N:17]([CH3:21])[C:18](Cl)=[O:19]>C(N(CC)CC)C>[Cl:14][C:4]1[CH:3]=[C:2]([NH:1][C:18](=[O:19])[N:17]([O:16][CH3:15])[CH3:21])[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:12][CH2:11][O:10][C:9]1=[O:13]

Participants

4

Reactant 2

HCID 2734926N-methoxy-N-methylcarbamoyl chlorideHCID 233373153-(4-Amino-2-chlorophenyl)-2-oxazolidinone

Product 1

HCID 23337319N'-(3-chloro-4-(2-oxo-3-oxazolidinyl)phenyl)-N-methoxy-N-methylurea

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

10.1 g of triethyamine was added to the solution of 1C, then 13.6 g of N-methoxy-N-methylcarbamoyl chloride was added drop-by-drop. After 12 hours at room temperature, the mixture was washed with water and extracted with ether. The extract was dried and the ether was evaporated under reduced pressure. The residue was chromatographed over silica gel to give 1, as a white solid, mp: 151°-153° C.

Workup

  1. washthe mixture was washed with water
  2. extractionextracted with ether
  3. customThe extract was dried
  4. customthe ether was evaporated under reduced pressure
  5. customThe residue was chromatographed over silica gel
  6. customto give 1

Sources & evidence

ORD record
ord-be16dce8df8346fbb304bce5a1408b3f
Source dataset
uspto-grants-1980_10
Patent number
US04226612

Reaction notes

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