Pyridine → Toluene-4-thiosulfonic acid S-(2-amino-5-tert-butyl-benzothiazol-6-yl)ester

HRID 1859544Notes

Reaction equation

HRID 1859544 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([SH:11])[C:8]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][C:5]=2[N:6]=1.N1C=CC=CC=1.[S:22](Br)([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23].C(Cl)(Cl)(Cl)Cl>CCOC(C)=O>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([S:11][S:22]([C:25]3[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[C:8]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:7][C:5]=2[N:6]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 5943Carbon TetrachlorideHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 225728932-Amino-5-tert-butyl-benzothiazole-6-thiol

Product 1

HCID 54107741Toluene-4-thiosulfonic acid S-(2-amino-5-tert-butyl-benzothiazol-6-yl)ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to General Method 15 using 2-amino-5-tert-butyl-benzothiazole-6-thiol (7.0 g, 29 mmol), pyridine (2.3 g, 29 mmol), tosyl bromide (6.9 g, 29 mmol), carbon tetrachloride (100 mL), and EtOAc (100 mL). The crude reaction mixture was purified by flash chromatography (5% EtOAc in hexanes to 50% EtOAc in hexanes as eluents). MS(APCI): 393 (M+H).

Workup

  1. customThe crude reaction mixture
  2. customwas purified by flash chromatography (5% EtOAc in hexanes to 50% EtOAc in hexanes as eluents)

Sources & evidence

ORD record
ord-17e00a8a4c6c4962966ccc24136b4e70
Source dataset
uspto-grants-2003_03
Patent number
US06528510B1

Reaction notes

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