Hydrochloric Acid → Benzoic acid 6-bromo-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl ester

HRID 643896노트

반응식

HRID 643896 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([OH:20])[C:8]([N:12]3[S:16](=[O:18])(=[O:17])[NH:15][C:14](=[O:19])[CH2:13]3)=[CH:9]2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])(O)=O.[Na+].Cl>CO.CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5](=[CH:4][CH:3]=1)[CH:6]=[C:7]([O:20][C:27](=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:8]([N:12]1[CH2:13][C:14](=[O:19])[NH:15][S:16]1(=[O:18])=[O:17])=[CH:9]2

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 177517615-(7-Bromo-3-hydroxynaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-oneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 86624016Benzoic acid 6-bromo-3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl ester

시약·촉매·용매 2

HCID 887Methanol용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-(7-bromo-3-hydroxynaphthalen-2-yl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (3) (0.998 g, 2.8 mmol) in MeOH is added KHCO3 (5.6 mL, 0.5M). To this salt in DMF (25 mL) at 0° C. is added potassium t-butoxide (2.94 mL, 1M). The reaction mixture is stirred for 1 min before benzoyl chloride (0.357 mL, 3.08 mmol) is added and the mixture is stirred for 1 min. Sat. NaHCO3 solution is added and it is acidified with 1 N HCl solution. The mixture is extracted with EtOAc, washed with brine and dried with Na2SO4. The organic layer is concentrated to give the title compound.

후처리

  1. additionis added
  2. extractionThe mixture is extracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. concentrationThe organic layer is concentrated

출처 및 근거

ORD 기록
ord-5b344af121c74b649a32ade99622172a
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700633B2

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