Water → Methyl 4-[(2-n-Butyl-5-formyl-4-iodo-1H-imidazol-5-yl)methyl]-1-naphthalene carboxylate

HRID 583554ノート

反応式

HRID 583554 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([C:11]1[NH:12][C:13]([CH:17]=[O:18])=[C:14]([I:16])[N:15]=1)[CH2:8][CH2:9][CH3:10].Br[CH2:20][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([C:31]([O:33][CH3:34])=[O:32])=[CH:23][CH:22]=1.O>CN(C)C=O>[CH2:7]([CH:11]1[N:15]=[C:14]([I:16])[C:13]([CH2:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24]([C:31]([O:33][CH3:34])=[O:32])=[CH:23][CH:22]=2)([CH:17]=[O:18])[NH:12]1)[CH2:8][CH2:9][CH3:10]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 103338131-Naphthalenecarboxylic acid, 4-(bromomethyl)-, methyl esterHCID 1784182622-Butyl-5-formyl-4-iodo-imidazole

生成物 1

HCID 86752288Methyl 4-[(2-n-Butyl-5-formyl-4-iodo-1H-imidazol-5-yl)methyl]-1-naphthalene carboxylate収率 85%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

A suspension of 29.53 g (0.214 mol) of powdered potassium carbonate, 60.00 g (0.214 mol) of 2-butyl-4-iodoimidazole-5-carboxaldehyde, and 65.68 g (0.235 mol) of methyl 4-bromomethylnaphthalene-1-carboxylate (E. A. Dixon, A. Fischer, and F. P. Robinson, Can. J. Chem. 59, 2629 (1981)) in 600 ml of dimethylformamide was stirred for 5 hours under argon at 70° C. An additional 6.56 g (0.0235 mol) of the bromomethyl ester was added and the suspension was stirred an additional 15 hours at 70° C. The mixture was poured into water and the solid which separated was collected by filtration, washed with water, and triturated several times with 250 ml of boiling methanol to give 86.8 g (85%) of a solid; mp 177.5-179° C.

後処理

  1. customthe solid which separated
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customtriturated several times with 250 ml of boiling methanol

出典と根拠

ORDレコード
ord-1ae8e9422c164de590015761fb3dd0c5
出典データセット
uspto-grants-1999_07
特許番号
US05929249

反応ノート

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