Sodium hydride → Methyl N-[4-(6-methoxybenzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate

HRID 1597821ノート

反応式

HRID 1597821 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[C:6]([CH3:15])[CH:5]=1.Br[CH2:17][C:18]1[S:19][C:20]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:21]=2[N:22]=1.[Cl-].[NH4+]>CN(C)C=O>[CH3:28][O:27][C:25]1[CH:24]=[CH:23][C:21]2[N:22]=[C:18]([CH2:17][O:3][C:4]3[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])[O:12][CH3:13])=[C:6]([CH3:15])[CH:5]=3)[S:19][C:20]=2[CH:26]=1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 107063232-Bromomethyl-6-methoxybenzothiazoleHCID 18932138methyl N-(4-hydroxy-2-methylphenyl)carbamate

生成物 1

HCID 18932427Methyl N-[4-(6-methoxybenzothiazol-2-ylmethoxy)-2-methylphenyl]carbamate収率 68%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

23 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 82 mg of methyl N-(4-hydroxy-2-methylphenyl)carbamate [prepared as described in Example 15(a) above] in 5 ml of dimethylformamide cooled in an ice-water bath. The resulting mixture was stirred at the same temperature for 15 minutes, and then 150 mg of 2-bromomethyl-6-methoxybenzothiazole [prepared as described in Example 6(a) above] were added. The temperature of the resulting mixture was elevated to room temperature and the mixture was stirred for 6 hours. At the end of this time, a saturated aqueous ammonium chloride solution was added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure and the resulting residue was purified by column chromatography through silica gel using a 2:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 110 mg (yield 68%) of the title compound as a solid having a melting point of 123° to 125° C.

後処理

  1. temperaturecooled in an ice-water bath
  2. customwas elevated to room temperature
  3. stirringthe mixture was stirred for 6 hours
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. extractionThe resulting extract
  6. washwas washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was then removed by evaporation under reduced pressure
  9. customthe resulting residue was purified by column chromatography through silica gel using a 2:1
  10. additionby volume mixture of hexane and ethyl acetate as the eluent

出典と根拠

ORDレコード
ord-f738c0f7f6624831af5c5282b48dc3e1
出典データセット
uspto-grants-1998_04
特許番号
US05736487

反応ノート

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