Benzyl Alcohol → HCID 15541461, compound

HRID 413781Notes

Reaction equation

HRID 413781 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:11]([O:15][C:16](=[O:29])[N:17]([C:19]1[CH:24]=[C:23](Cl)[CH:22]=[CH:21][C:20]=1[N+:26]([O-])=O)[CH3:18])([CH3:14])([CH3:13])[CH3:12]>CN(C=O)C>[C:11]([O:15][C:16](=[O:29])[N:17]([C:19]1[CH:24]=[C:23]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:22]=[CH:21][C:20]=1[NH2:26])[CH3:18])([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 15541461HCID 15541461, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To anhydrous DMF were added benzyl alcohol (2.48 ml) and 55% NaH (1.05 g) and then N-(2-nitro-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (5.73 g) was added in small portions. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated. The resulting residue was stirred in a mixture of dioxane (100 ml), water (10 ml), sodium hydrosulfite (20.9 g) and sodium hydrogencarbonate (21.0 g) at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and water and the extract was dried over anhydrous sodium sulfate and concentrated. The resulting residue was chromatographed on a silica gel column using ethyl acetate/n-hexane (1/2) as the eluant to afford the title compound (2.29 g). melting point: 86-89° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. stirringThe resulting residue was stirred in a mixture of dioxane (100 ml), water (10 ml), sodium hydrosulfite (20.9 g) and sodium hydrogencarbonate (21.0 g) at room temperature for 1 hour
  6. customThe reaction mixture was partitioned between ethyl acetate and water
  7. dry with materialthe extract was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe resulting residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-ad1cf0fc74bc46939ca73c19b1893a31
Source dataset
uspto-grants-2003_05
Patent number
US06569877B2

Reaction notes

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