Acetone → Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-hydroxymethylcarbamate

HRID 1597804Notes

Reaction equation

HRID 1597804 reaction equation
C[C:2](C)=[O:3].[S:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:26])[O:24][CH3:25])=[C:18]([CH3:27])[CH:17]=1.C=O>C(=O)([O-])[O-].[K+].[K+].O>[S:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]([CH2:2][OH:3])[C:23](=[O:26])[O:24][CH3:25])=[C:18]([CH3:27])[CH:17]=1

Participants

6

Reactant 3

HCID 180AcetoneHCID 712FormaldehydeHCID 18932257methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate

Product 1

HCID 18932060Methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]-N-hydroxymethylcarbamateYield 73.4%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of 130 ml of acetone and 0.5 ml of water was added to a mixture of 10.01 g of methyl N-[4-(benzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate (prepared as described in Example 21(c) below) and 5.0 g of paraformaldehyde at room temperature. 0.30 g of potassium carbonate were added to the resulting mixture and the mixture was then stirred for 12 hours at 30° C. while subjected to ultrasonic irradiation. At the end of this time the reaction mixture was filtered and the solvent was removed from the filtrate by evaporation under reduced pressure to give a residue which was purified by column chromatography through silica gel, using a gradient of dichloromethane and acetone as the eluent, gradually changing from a 9:1 by volume mixture of dichloromethane and acetone to a final 4:1 by volume mixture, to give 8.02 g (yield 73.4%) of the title compound as a solid having a melting point of 121°-123° C.

Workup

  1. customwhile subjected to ultrasonic irradiation
  2. filtrationAt the end of this time the reaction mixture was filtered
  3. customthe solvent was removed from the filtrate by evaporation under reduced pressure
  4. customto give a residue which
  5. customwas purified by column chromatography through silica gel
  6. additiongradually changing from a 9:1 by volume mixture of dichloromethane and acetone to a final 4:1 by volume mixture

Sources & evidence

ORD record
ord-05a8f9404d564280b1d3245ced0a3dca
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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