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Benzocaine → Ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoate

HRID 1006048
ノート
印刷プレビュー

反応式

HRID 1006048 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16][C:17]([OH:19])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[NH2:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1.CN(C=O)C.ClCCl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[CH2:16][C:17]([NH:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:34][CH:35]=1)=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 2337BenzocaineHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 33070112-[2-(Benzyloxy)-5-bromophenyl]acetic acid

生成物 1

HCID 54475189Ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoate収率 42.9%

試薬・触媒・溶媒 3

HCID 6228
Dimethylformamide
触媒
HCID 1140Toluene溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
80 °C

実験手順

To a mixture of 2-benzyloxy-5-bromophenylacetic acid (3.2 g) in toluene (100 ml) was added thionyl chloride (1.0 ml) and DMF (3 drops). The reaction was stirred at 80° C. for 1 hour and cooled to ambient temperature ethyl 4-aminobenzoate (2.0 g) and triethylamine (2 ml) were added to the reaction mixture with stirring. After standing for 18 hours, the mixture was diluted with dichloromethane and washed with water, 1N HCl solution, water and sautrated aqueous NaHCO3 solution. The organic extract was dried (MgSO4), filtered and evaporated and the residue purified by trituration with diethyl ether to give ethyl 4-[2-benzyloxy-5-bromophenylacetamido]benzoate (2.0 g) mpt. 174-176° C.

後処理

  1. additionwere added to the reaction mixture
  2. stirringwith stirring
  3. waitAfter standing for 18 hours
  4. washwashed with water, 1N HCl solution, water
  5. extractionThe organic extract
  6. dry with materialwas dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated
  9. customthe residue purified by trituration with diethyl ether

出典と根拠

ORDレコード
ord-d102cd53a21544c0ba6984a04474a89d
出典データセット
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06787562B2

反応ノート

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