Benzoyl chloride → HCID 53746038, compound

HRID 2187167Notes

Reaction equation

HRID 2187167 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:13][C:14](=[S:26])[NH:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=2)[CH:5]=[C:6]([Cl:12])[C:7]=1[O:8][CH2:9][CH2:10][OH:11].[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>N1C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:14](=[S:26])[NH:13][C:4]2[CH:3]=[C:2]([Cl:1])[C:7]([O:8][CH2:9][CH2:10][O:11][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[C:6]([Cl:12])[CH:5]=2)=[CH:17][CH:18]=1)(=[O:25])[CH3:24]

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 15907988HCID 15907988, compound

Product 1

HCID 53746038HCID 53746038, compound

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To an ice cooled solution of N-(4-{3-[3,5-dichloro-4-(2-hydroxy-ethoxy)-phenyl]-thioureido}-phenyl)-acetamide (0.20 g) in pyridine (2 mL) and tetrahydrofuran (0.5 mL) is added benzoyl chloride (0.08 g) and the mixture is stirred at 0° C. for 1.5 hours. The mixture is then diluted with ethyl acetate, washed successively two times with 2% aqueous hydrochloric acid, once with saturated aqueous sodium chloride, then dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure the residue is chromatographed over silica gel (5% methanol in dichloromethane is used as the eluant) and product containing fractions are combined, evaporated under reduced pressure, and the residue is recrystallized from acetone-hexanes to provide the desired product as a white powder.

Workup

  1. washwashed successively two times with 2% aqueous hydrochloric acid
  2. dry with materialonce with saturated aqueous sodium chloride, then dried over anhydrous sodium sulfate
  3. customAfter removal of the solvent under reduced pressure the residue
  4. customis chromatographed over silica gel (5% methanol in dichloromethane
  5. additioncontaining fractions
  6. customevaporated under reduced pressure
  7. customthe residue is recrystallized from acetone-hexanes

Sources & evidence

ORD record
ord-26c669df772d4828b1898f82e7b1934d
Source dataset
uspto-grants-2002_06
Patent number
US06407249B1

Reaction notes

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