Quinone → 2-Amino-6-benzothiazolol

HRID 333716Notes

Reaction equation

HRID 333716 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[C:5]1(=O)[CH:10]=[CH:9][C:8](=[O:11])[CH:7]=[CH:6]1>C(O)C.Cl>[NH2:1][C:2]1[S:3][C:10]2[CH:9]=[C:8]([OH:11])[CH:7]=[CH:6][C:5]=2[N:4]=1

Participants

5

Reactant 2

HCID 4650QuinoneHCID 2723790Thiourea

Product 1

HCID 334622-Amino-6-benzothiazolol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

The intermediate 2-amino-1,3-benzothiazol-6-ol was prepared according to a slightly modified literature procedure by Lau and Gompf: J. Org. Chem. 1970, 35, 4103-4108. To a stirred solution of thiourea (7.6 g, 0.10 mol) in a mixture of 200 mL ethanol and 9 mL concentrated hydrochloric acid was added a solution of 1,4-benzoquinone (21.6 g, 0.20 mol) in 400 mL of hot ethanol. The reaction was stirred for 24 hours at room temperature and then concentrated to dryness. The residue was triturated with hot acetonitrile and the resulting solid was filtered and dried.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue was triturated with hot acetonitrile
  3. filtrationthe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-51fa00df3d05479481cc19f73089b8bf
Source dataset
uspto-grants-2014_11
Patent number
US08883783B2

Reaction notes

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