Methyl Isocyanate → HCID 16225956, compound

HRID 2355224Notes

Reaction equation

HRID 2355224 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][NH2:22])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH3:23][N:24]=[C:25]=[O:26]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH2:15][CH2:16][C@H:17]([CH2:21][NH:22][C:25]([NH:24][CH3:23])=[O:26])[O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 58869130HCID 58869130, compound

Product 1

HCID 16225956HCID 16225956, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of C—[(R)-7-(3-Fluoro-benzenesulfonyl)-chroman-2-yl]-methylamine (0.130 g, 0.405 mmol) in methylene chloride (10 mL) at 0° C. was added methyl isocyanate (0.115 g, 2.03 mmol). The mixture was stirred at room temperature for one hour, and was then quenched by addition of MeOH. The mixture was partitioned between water and methylene chloride, and the organic phase was washed with water and brine, dried (Na2SO4), filtered and contrated under reduced pressure. Purification of the residue by flash chromatography (hexanes:EtOAc 1:9) gave 0.153 g of 1-[(R)-7-(3-fluoro-benzenesulfonyl)-chroman-2-ylmethyl]-3-methyl-urea as a foam. MS (M+H)=379.

Workup

  1. customwas then quenched by addition of MeOH
  2. customThe mixture was partitioned between water and methylene chloride
  3. washthe organic phase was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customPurification of the residue by flash chromatography (hexanes:EtOAc 1:9)

Sources & evidence

ORD record
ord-1bebd3776c6d4452a9d913c16afc16fe
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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