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

HRID 1416228

반응식

HRID 1416228 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-01dfcac74ca346daa5c0a46517441c14
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05912258

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