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Sulfuric Acid → 2-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-5,6,7,8-tetrahydro-thiazolo[4,5-c]azepin-4-one

HRID 1433076
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HRID 1433076 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]4[S:21][C:22]5[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[C:23]=5[N:24]=4)[C:15](=[O:30])[CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:31]=1.S(=O)(=O)(O)O.[N-:37]=[N+]=[N-].[Na+].C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][C:20]4[S:21][C:22]5[CH2:28][CH2:27][CH2:26][NH:37][C:25](=[O:29])[C:23]=5[N:24]=4)[C:15](=[O:30])[CH2:14]3)(=[O:11])=[O:12])[S:7][C:6]=2[CH:31]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 670150242-[4-(6-chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-6,7-dihydro-5H-benzothiazol-4-one

생성물 1

HCID 670148362-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-5,6,7,8-tetrahydro-thiazolo[4,5-c]azepin-4-one

시약·촉매·용매

2
HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

2-[4-(6-Chloro-benzo[b]thiophene-2-sulfonyl)-2-oxo-piperazin-1-ylmethyl]-6,7-dihydro-5H-benzothiazol-4-one (60 mg, 0.12 mmol) is dissolved in CHCl3 (4 mL) and sulfuric acid (0.5 mL) is added with vigorous stirring. Sodium azide (25 mg 0.4 mmol) is added and the reaction is stirred 1¾ h. The reaction is then added dropwise to a rapidly stirring mixture of K2CO3/H20/CH2Cl2. The organic phase is separated and washed with water, dried (MgSO4) and concentrated. The residue is purified by column chromatography (silica, 2% to 6% MeOH/CH2Cl2) to provide a mixture of two products.

후처리

  1. additionThe reaction is then added dropwise to
  2. stirringa rapidly stirring
  3. customThe organic phase is separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue is purified by column chromatography (silica, 2% to 6% MeOH/CH2Cl2)
  8. customto provide
  9. additiona mixture of two products

출처 및 근거

ORD 기록
ord-1f6e5c5f31934847adb4f29d1e8ce267
출처 데이터셋
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07612075B2

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