Methyl Isocyanate → (Z)-N-{2-[5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-yl]ethyl}-N-hydroxy-N'-methylurea

HRID 1420728Notes

Reaction equation

HRID 1420728 reaction equation
[NH:1]([CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:14])[CH:12]=2)/[C:7](=[CH:15]\[C:16]2[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=2)/[C:6]=1[CH3:24])[OH:2].[CH3:25][N:26]=[C:27]=[O:28]>C1COCC1>[F:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:15]\[C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][CH:17]=1)/[C:6]([CH3:24])=[C:5]2[CH2:4][CH2:3][N:1]([OH:2])[C:27]([NH:26][CH3:25])=[O:28]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 86745522(Z)-3-(2-hydroxaminoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

Product 1

HCID 10135501(Z)-N-{2-[5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-yl]ethyl}-N-hydroxy-N'-methylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (Z)-3-(2-hydroxaminoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)-indene from Example 3, Method A, Step 4 (34 mg, 0.1 mmol) in THF (0.5 mL), there was added methyl isocyanate (11.4 mg, 0.2 mmol) and the mixture stirred at room temperature for 1 hour. The solvent was evaporated and the residue triturated with hexane and filtered to afford the title product as a yellow-orange solid, mp: dec 138° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue triturated with hexane
  3. filtrationfiltered

Sources & evidence

ORD record
ord-a66c1b8b6a8e4002bf8b478802b47959
Source dataset
uspto-grants-2000_06
Patent number
US06071934

Reaction notes

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