1-Chloro-2-isothiocyanatobenzene → HCID 58725959, compound

HRID 970270Notes

Reaction equation

HRID 970270 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([NH:13][NH2:14])=[O:12])=[O:6].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[S:30]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11]([NH:13][NH:14][C:29]([NH:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[Cl:21])=[S:30])=[O:12])=[O:6]

Participants

4

Reactant 2

HCID 1231711-Chloro-2-isothiocyanatobenzeneHCID 25219120HCID 25219120, compound

Product 1

HCID 58725959HCID 58725959, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 200 mg (0.69 mmol) of 3-(3-chlorobenzamido)benzhydrazide in 2.5 mL of tetrahydrofuran was added 175 mg (135 μL, 1.04 mmol) of 2-chlorophenyl isothiocyanate. The reaction was stirred at room temperature overnight. After concentration by rotoevaporation, the residue was purified by preparative HPLC to give 243 mg (0.53 mmol, 77% yield) of 1-[3-(3-chlorobenzamido)benzoyl]-4-(2-chlorophenyl)thiosemicarbazide. 1H NMR (CDCl3): δ7.28 (d of t, 1H), 7.35 (d of t, 1H), 7.99 (t, 1H), 8.34 (br s, 1H), and 8.98 ppm (br s, 1H). MS m/z: 459.0 (M+H).

Workup

  1. concentrationAfter concentration by rotoevaporation
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-d3926a1bf1e04e66927e21406e1bdecd
Source dataset
uspto-grants-2007_12
Patent number
US07312181B2

Reaction notes

Loading…