Acetic Acid → Benzothiazole

HRID 1953463Notes

Reaction equation

HRID 1953463 reaction equation
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2C=CN1[S:11]([C:14]1[CH:19]=[CH:18][N:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16](=[O:26])[C:15]=1[N:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])(=[O:13])=[O:12].C(O)(=O)C.C1C(=O)[N:50]([Cl:53])[C:48](=O)C1>C(O)C.C(Cl)Cl.[Zn]>[Cl:53][S:11]([C:14]1[CH:19]=[CH:18][N:17]([CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16](=[O:26])[C:15]=1[N:27]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])(=[O:13])=[O:12].[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:50]=[CH:48]1

Participants

8

Reactant 3

HCID 176Acetic AcidHCID 31398ChlorosuccinimideHCID 232982454-(2-benzothiazinylsulfonyl)-3-(N,N-di-t-butoxycarbonylamino)-1-ethyloxycarbonylmethyl-2-pyridinone

Product 2

HCID 7222BenzothiazoleHCID 232982504-Chlorosulfonyl-3-(N,N-di-t-butoxycarbonylamino)-1-ethyloxycarbonylmethyl-2-pyridinone

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

Zinc powder (6.93 g, 106 mmol) was added to a stirred mixture of 4-(2-benzothiazinylsulfonyl)-3-(N,N-di-t-butoxycarbonylamino)-1-ethyloxycarbonylmethyl-2-pyridinone (3.94 g, 6.48 mmol) and acetic acid (8.73 mL) in ethanol (63 mL). After 16 h, the reaction mixture was filtered and evaporated in vacuo at rt. NCS (0.952 g, 7.13 mmol) was added to a stirred mixture of this residue in methylene chloride (100 mL) at -5° C. After 15 min the reaction was warmed to rt and after a further 40 min the reaction was filtered through celite and evaporated in vacuo to give the title compound contaminated with benzothiazole (1 equivalent) as a yellow solid;

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated in vacuo at rt
  3. filtrationwas filtered through celite
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-b8f685bd0879460e9c4267a8fc121b7a
Source dataset
uspto-grants-2000_09
Patent number
US06117888

Reaction notes

Loading…