Triethylamine → alpha-[[[(2-Acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcohol

HRID 1768826ノート

反応式

HRID 1768826 の反応式
Cl.[NH2:2][CH2:3][CH:4]([OH:15])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1.[C:16]([NH:19][C:20]1[S:21][CH:22]=[C:23]([CH:25]=O)[N:24]=1)(=[O:18])[CH3:17].C(N(CC)CC)C.[BH4-].[Na+]>CO>[C:16]([NH:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25][NH:2][CH2:3][CH:4]([OH:15])[C:5]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=2)[N:24]=1)(=[O:18])[CH3:17]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 128889092-Amino-1-(3,4-dimethoxyphenyl)ethan-1-ol hydrochlorideHCID 14931749N-(4-Formyl-1,3-thiazol-2-YL)acetamide

生成物 1

HCID 14719582alpha-[[[(2-Acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcohol収率 82%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

α-(Aminomethyl)-3,4-dimethoxybenzyl alcohol hydrochloride (2.88 g) and 2-acetamido-4-formyl-thiazole (2.1 g) were suspended in 14 ml methanol, and 1.8 ml triethylamine was added dropwise to this suspension with stirring. The resulting solution was heated under reflux for 30 minutes, and 0.70 g sodium borohydride was added in small portions with stirring under ice cooling. The crystals which separated out were collected by filtration, washed with water and methanol in that order and vaccum-dried, giving 3.55 g of α-[[[(2-acetamido-4-thiazolyl)methyl]amino]methyl]-3,4-dimethoxybenzyl alcohol, m.p. 204°-206° C.

後処理

  1. temperatureThe resulting solution was heated
  2. temperatureunder reflux for 30 minutes
  3. stirringwith stirring under ice cooling
  4. customThe crystals which separated out
  5. filtrationwere collected by filtration
  6. washwashed with water and methanol in that order
  7. customvaccum-dried

出典と根拠

ORDレコード
ord-8c10de0dc20748b68c90138fcc325f65
出典データセット
uspto-grants-1995_01
特許番号
US05378849

反応ノート

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