2-Chloroethyl isocyanate → HCID 18789690, compound

HRID 1106772Notes

Reaction equation

HRID 1106772 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[Cl:14][CH2:15][CH2:16][N:17]=[C:18]=[O:19]>C1COCC1>[Cl:14][CH2:15][CH2:16][NH:17][C:18](=[O:19])[NH:1][C:2]1[C:3]([CH3:13])=[C:4]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 16777787HCID 16777787, compound

Product 1

HCID 18789690HCID 18789690, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of N-(3-amino-2-methyl-phenyl)-methanesulfonamide (1.5 g, from Example 6, part 1) in THF (30 mL) was added 2-chloroethylisocyanate (0.7 mL) dropwise at 0° C. The reaction mixture was slowly warmed to room temperature and stirred overnight. The precipitate was filtered, rinsed with THF, and dried to give N-{3-[3-(2-chloro-ethyl)-ureido]-2-methyl-phenyl}-methanesulfonamide (1.8 g). To the above compound (1.7 g) in acetonitrile (100 mL) was added potassium fluoride (40 wt. % on alumina) (3.5 g). The mixture was heated at 80° C. for 8 hr and filtered, washed with methanol . The filtrate was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with methanol:dichloromethane (5:95) to afford N-[2-methyl-3-(oxazolidin-2-ylideneamino)-phenyl]-methanesulfonamide. This was converted to oxalate salt (0.5 g), mp 124-140° C. in a manner similar to that described above in Example 7, part 4.

Workup

  1. filtrationThe precipitate was filtered
  2. washrinsed with THF
  3. customdried

Sources & evidence

ORD record
ord-97644bba3bbd49a28d2a7eacabb9afd7
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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