Benzoyl isothiocyanate → 1-(2-Amino-benzothiazol-5-yl)-3-benzoyl-thiourea

HRID 723952Notes

Reaction equation

HRID 723952 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([NH2:10])=[N:7][C:6]=2[CH:11]=1.[C:12]([N:20]=[C:21]=[S:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[NH2:10][C:8]1[S:9][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:21]([NH:20][C:12](=[O:19])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[S:22])=[CH:11][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 7685251,3-Benzothiazole-2,5-diamine

Product 1

HCID 100421591-(2-Amino-benzothiazol-5-yl)-3-benzoyl-thiourea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of anhydrous THF (6.7 mL) was added 5-amino-benzothiazol-2-ylamine (Example 16, 100 mg, 0.61 mmol) and benzoyl isothiocyanate (0.08 mL, 1 equiv). The resulting mixture was stirred at room temperature for 2 hours, after which the solvent was evaporated and the residue was washed with a 1:1 mixture of ether/hexanes (0.164 g, 83%). 1H NMR (DMSO d6) δ: 12.61 (s, 1H), 11.53 (s, 1H), 7.99 (d, 1H, J=3.9 Hz), 7.76 (s, 1H), 7.69–7.65 (m, 2H), 7.59–7.53 (m, 4H), 7.25–7.23 (d, 1H, J=3.9 Hz); MS (ESI) 328.8 (M+1, 100%).

Workup

  1. customafter which the solvent was evaporated
  2. washthe residue was washed with a 1:1 mixture of ether/hexanes (0.164 g, 83%)

Sources & evidence

ORD record
ord-1afc06bd929541f28f03a93a0aca4b46
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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