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

HRID 643896ノート

反応式

HRID 643896 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5b344af121c74b649a32ade99622172a
出典データセット
uspto-grants-2010_04
特許番号
US07700633B2

反応ノート

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