Water → Carboxyamidotriazole

HRID 280654노트

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HRID 280654 반응식
[NH2:1][C:2]1[NH:6][N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8].[H-].[Na+].[Cl:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([C:19]2[C:26]([Cl:27])=[CH:25][C:22]([CH2:23]Br)=[CH:21][C:20]=2[Cl:28])=[O:18])=[CH:15][CH:14]=1.O>CN(C)C=O.C(O)(=O)C>[NH2:1][C:2]1[N:6]([CH2:23][C:22]2[CH:21]=[C:20]([Cl:28])[C:19]([C:17](=[O:18])[C:16]3[CH:15]=[CH:14][C:13]([Cl:12])=[CH:30][CH:29]=3)=[C:26]([Cl:27])[CH:25]=2)[N:5]=[N:4][C:3]=1[C:7]([NH2:9])=[O:8]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydride2회HCID 136496564-(4-Chlorobenzoyl)-3,5-dichlorobenzyl bromideHCID 178513860HCID 178513860, 화합물

생성물 1

HCID 108144Carboxyamidotriazole수율 17%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매

실험 절차

A stirred ambient temperature solution of 5-amino-1,2,3-triazole-4-carboxamide (630 mg, 4.96 mmol) in dry dimethylformamide (20 ml) was treated in one portion with sodium hydride (230 mg of a 50% suspension in mineral oil, 115 mg NaH, 4.79 mmol). After 15 min. solid 4-(4-chlorobenzoyl)-3,5-dichlorobenzyl bromide was added in one portion. The mixture was stirred 1 hour, poured into water (20 ml), acidified to pH 6 with glacial acetic acid, and filtered. The solid was washed three times with water and dissolved in dichloromethane. The layers were separated and the organic phase was dried over anhydrous magnesium sulfate and evaporated under vacuum. The residue was chromatographed on a column of silica gel (200 g) eluted with 97:3 (v/v) dichloromethane-methanol to provide 351 mg (17%) 5-amino-1-(4-[4-chlorobenzoyl]-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide.

후처리

  1. filtrationfiltered
  2. washThe solid was washed three times with water
  3. dissolutiondissolved in dichloromethane
  4. customThe layers were separated
  5. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  6. customevaporated under vacuum
  7. customThe residue was chromatographed on a column of silica gel (200 g)
  8. washeluted with 97:3 (v/v) dichloromethane-methanol

출처 및 근거

ORD 기록
ord-ad84160f5aa440c2886ec6b0f5474767
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04590201

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