1-Hydroxybenzotriazole → 2-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide

HRID 1934644

反応式

HRID 1934644 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[O:14]1[C:18]2[CH:19]=[CH:20][C:21]([CH2:23][NH2:24])=[CH:22][C:17]=2[O:16][CH2:15]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:24][CH2:23][C:21]1[CH:20]=[CH:19][C:18]2[O:14][CH2:15][O:16][C:17]=2[CH:22]=1)=[O:6]

参加物

6

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 75799Benzo-1,3-dioxole-5-methylamineHCID 2809972-Fluoro-5-nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 224676412-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide収率 86.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2-fluoro-5-nitrobenzoic acid (1.00 g), (1,3-benzodioxol-5-ylmethyl)amine (980 mg), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (1.55 g) and 1-hydroxybenzotriazole (1.09 g) in anhydrous dimethylformamide (10 mL) was stirred for 40 hours at ambient temperature. The mixture was partitioned between water and ethyl acetate. The separated organic layer was washed with an aqueous saturated sodium bicarbonate solution, 1N-hydrochloric acid, water and brine. Then, the resultant was dried over magnesium sulfate and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 2-fluoro-5-nitro-N-(1,3-benzodioxol-5-ylmethyl)benzamide as yellow powders (1.48 g).

後処理

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe separated organic layer was washed with an aqueous saturated sodium bicarbonate solution, 1N-hydrochloric acid, water and brine
  3. dry with materialThen, the resultant was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diisopropyl ether

出典と根拠

ORDレコード
ord-829a96a6ccff41a995f08c54de850f1f
出典データセット
uspto-grants-2002_05
特許番号
US06384080B1

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