Hydrochloric Acid → 4-(4-Carboxyphenyl)-1-(3,5-dichloro-2-hydroxybenzylidene)-3-thiosemicarbazide

HRID 1294723Notes

Reaction equation

HRID 1294723 reaction equation
Cl.[C:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[S:15])[NH:13][NH2:14])=[CH:7][CH:6]=1)([OH:4])=[O:3].[Cl:16][C:17]1[C:18]([OH:26])=[C:19]([CH:22]=[C:23]([Cl:25])[CH:24]=1)[CH:20]=O.O>CN(C)C=O>[C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[S:15])[NH:13][N:14]=[CH:20][C:19]2[CH:22]=[C:23]([Cl:25])[CH:24]=[C:17]([Cl:16])[C:18]=2[OH:26])=[CH:9][CH:10]=1)([OH:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 666603,5-DichlorosalicylaldehydeHCID 27573784-(4-Carboxyphenyl)-3-thiosemicarbazide

Product 1

HCID 1363804484-(4-Carboxyphenyl)-1-(3,5-dichloro-2-hydroxybenzylidene)-3-thiosemicarbazideYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Concentrated aqueous hydrochloric acid (1 mL) was added to a stirred solution of 4-(4-carboxyphenyl)-3-thiosemicarbazide (213 mg, 1.00 mmol) and 3,5-dichloro-2-hydroxybenzaldehyde (198 mg, 1.04 mmol) in dimethylformamide (20 mL). The mixture was stirred for 18 h, water was added and the precipitate filtered, washed (water) and dried to give the title compound (212 mg, 55%) as a solid. MS (ES−) m/e 382, 384 [M−H]-.

Workup

  1. filtrationthe precipitate filtered
  2. washwashed (water)
  3. customdried

Sources & evidence

ORD record
ord-f9b799c2f3c249ceb8f72aaca2293dc8
Source dataset
uspto-grants-2007_07
Patent number
US07241783B2

Reaction notes

Loading…