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

HRID 2081872ノート

反応式

HRID 2081872 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>[CH3:34][O:33][C:31]([C:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([CH2:20][N:12]2[C:13]([CH:17]=[O:18])=[C:14]([I:16])[N:15]=[C:11]2[CH2:7][CH2:8][CH2:9][CH3:10])=[CH:22][CH:23]=1)=[O:32]

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 19936811methyl-4-[(2-butyl-5-formyl-4-iodo-1H-imidazol-1-yl)methyl]naphthalene-1-carboxylate収率 85.2%

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 reaction mixture was poured into water and the resulting solid 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. filtrationthe resulting solid was collected by filtration
  2. washwashed with water
  3. customtriturated several times with 250 mL of boiling methanol

出典と根拠

ORDレコード
ord-ad302fa673694430be9f95b736cf1b84
出典データセット
uspto-grants-1993_02
特許番号
US05185351

反応ノート

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