2,6-Benzothiazolediamine → N-[(2-Amino-1,3-benzothiazol-6-yl)carbamothioyl]benzamide

HRID 723944Notes

Reaction equation

HRID 723944 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:12]1[C:16]2[CH:17]=[C:18]([NH2:21])[CH:19]=[CH:20][C:15]=2[N:14]=[C:13]1[NH2:22]>C1COCC1>[NH2:22][C:13]1[S:12][C:16]2[CH:17]=[C:18]([NH:21][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[S:11])[CH:19]=[CH:20][C:15]=2[N:14]=1

Participants

4

Reactant 2

HCID 215042,6-BenzothiazolediamineHCID 68284Benzoyl isothiocyanate

Product 1

HCID 21878462N-[(2-Amino-1,3-benzothiazol-6-yl)carbamothioyl]benzamideYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzoylisothiocyanate (0.12 mL, 0.91 mmol) was added dropwise to a solution of benzothiazole-2,6-diamine (Example 1, 150 mg, 0.91 mmol) in 10 mL of THF at room temperature. The mixture was stirred at room temperature for 7 hours and then concentrated. The residue was washed with a 1:1 mixture of Et2O and hexanes. Yield: 97.3%, 1H-NMR (DMSO-d6): δ 12.65 (s, 1H); 11.55 (s, 1H); 8.00 (m, 3H); 7.60 (m, 5H); 7.38 (m, 2H).

Workup

  1. concentrationconcentrated
  2. washThe residue was washed with a 1:1 mixture of Et2O and hexanes

Sources & evidence

ORD record
ord-79b5fbdda1824fabbf4a8db9013f56f8
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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