Water → (Z)-N-{2-[5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-yl]ethyl}-N-hydroxyurea

HRID 2371478Notes

Reaction equation

HRID 2371478 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22][NH:23][OH:24].C[Si]([N:29]=[C:30]=[O:31])(C)C.O.C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22][N:23]([OH:24])[C:30]([NH2:29])=[O:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70696Trimethylsilyl isocyanateHCID 86745522(Z)-3-(2-hydroxaminoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

Product 1

HCID 10221633(Z)-N-{2-[5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-yl]ethyl}-N-hydroxyurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the hydroxylamine intermediate from Step 4 (1.62 g, 4.7 mmol) in THF (15 mL) there was added 85% trimethylsilyl isocyanate (954 mg, 7.25 mmol). The mixture was stirred at room temperature for 30 minutes. Water (10 mL) was added and stirring was continued for a further 10 minutes. Ethyl acetate was then added, the organic layer was decanted, washed with brine, dried over MgSO4 and evaporated to dryness. The residue was triturated with ether and filtered to afford the pure title product as a yellow solid, mp: 149° C. dec.

Workup

  1. stirringstirring
  2. waitwas continued for a further 10 minutes
  3. customthe organic layer was decanted
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe residue was triturated with ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-0af7910501f644da8b256e82dd95481e
Source dataset
uspto-grants-1992_03
Patent number
US05093356

Reaction notes

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