Sodium hydride → 2-(4-Isopropyloxybenzoyl)amino-5-diethylaminoethylthio-1,3,4-thiadiazole

HRID 1416228

反応式

HRID 1416228 の反応式
[H-].[Na+].[NH2:3][C:4]1[S:5][C:6]([S:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:7][N:8]=1.[CH:17]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)([CH3:19])[CH3:18].C(N1C=CN=C1)(N1C=CN=C1)=O>O1CCCC1>[CH:17]([O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH:3][C:4]2[S:5][C:6]([S:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:7][N:8]=2)=[O:26])=[CH:23][CH:22]=1)([CH3:19])[CH3:18]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 729724-Isopropoxybenzoic acidHCID 3145445-{[2-(Diethylamino)ethyl]sulfanyl}-1,3,4-thiadiazol-2-amine

生成物 1

HCID 99086522-(4-Isopropyloxybenzoyl)amino-5-diethylaminoethylthio-1,3,4-thiadiazole収率 61.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Sodium hydride (0.6 g) and 2-amino-5-diethylaminoethylthio-1,3,4-thiadiazole (2.3 g) were stirred in tetrahydrofuran (30 ml) for 30 minutes while being cooled with ice. 4-Isopropyloxybenzoic acid (1.8 g) and carbonyldiimidazole (1.8 g) were stirred in tetrahydrofuran (30 ml) for 30 minutes at room temperature and the mixture was added to the former reaction mixture. The mixture was stirred for 4 hours at room temperature, and then concentrated under a vacuum. The residue, with water added thereto, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=20:1). The resulting solid was recrystallized from n-hexane/ethanol, thereby yielding 2.4 g of the aimed compound.

後処理

  1. temperaturewhile being cooled with ice
  2. additionthe mixture was added to the former reaction mixture
  3. concentrationconcentrated under a vacuum
  4. additionThe residue, with water added
  5. extractionwas extracted with ethyl acetate
  6. dry with materialThe extract was dried over sodium sulfate anhydride
  7. concentrationconcentrated under a vacuum
  8. customThe residue was purified by silica gel column chromatography (chloroform:methanol=20:1)
  9. customThe resulting solid was recrystallized from n-hexane/ethanol

出典と根拠

ORDレコード
ord-01dfcac74ca346daa5c0a46517441c14
出典データセット
uspto-grants-1999_06
特許番号
US05912258

関連ノート

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