Oxalyl chloride → HCID 53752128, compound

HRID 1602489Notes

Reaction equation

HRID 1602489 reaction equation
C(Cl)(=O)C(Cl)=O.[S:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]=[CH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][CH:19]=1.Cl.[NH2:28][C:29]1[CH:34]=[C:33]([CH2:35][CH2:36][CH2:37][S:38]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)(=[O:40])=[O:39])[CH:32]=[CH:31][C:30]=1[OH:48]>CN(C)C=O.ClCCl.N1C=CC=CC=1>[S:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH:16]=[CH:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:28][C:29]2[CH:34]=[C:33]([CH2:35][CH2:36][CH2:37][S:38]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=3)(=[O:40])=[O:39])[CH:32]=[CH:31][C:30]=2[OH:48])=[O:24])=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 65578Oxalyl chlorideHCID 52170324-[2-(2-Benzothiazolyl)vinyl]benzoic acidHCID 196115102-Amino-4-[3-(4-chlorophenylsulfonyl)propyl]phenol hydrochloride

Product 1

HCID 53752128HCID 53752128, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

At -78° C., oxalyl chloride (135 mg, 1.06 mmol) was added to a mixture of 4-[2-(2-benzothiazolyl)vinyl]benzoic acid (247 mg, 0.88 mmol), dimethylformamide (one drop) and dichloromethane (10 ml), and the resulting mixture was stirred at room temperature for 2 hours and then concentrated under reduced pressure. Under ice-cooling, the resulting compound was gradually added to a mixture of 2-amino-4-[3-(4-chlorophenylsulfonyl)propyl]phenol hydrochloride (320 mg, 0.88 mmol), pyridine (3 ml) and dichloromethane (10 ml), and the resulting mixture was stirred at room temperature for 12 hours. The reaction solution was concentrated under reduced pressure, water was added to the resulting residue, and the mixture was heated until reflux and then cooled. Then, the solid material formed was collected by filtration and dried under reduced pressure. Ethanol (10 ml) was added to the resulting solid material, and the mixture was heated until reflux and then cooled. The crystals formed were collected by filtration and dried under reduced pressure to give 4-[2-(2-benzothiazolyl)vinyl]-5'-[3-(4-chlorophenylsulfonyl)propyl]-2'-hydroxybenzanilide (335 mg, 0.57 mmol, 65%) as colorless crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. temperatureUnder ice-cooling
  3. stirringthe resulting mixture was stirred at room temperature for 12 hours
  4. concentrationThe reaction solution was concentrated under reduced pressure, water
  5. additionwas added to the resulting residue
  6. temperaturethe mixture was heated
  7. temperatureuntil reflux
  8. temperaturecooled
  9. customThen, the solid material formed
  10. filtrationwas collected by filtration
  11. customdried under reduced pressure
  12. additionEthanol (10 ml) was added to the resulting solid material
  13. temperaturethe mixture was heated
  14. temperatureuntil reflux
  15. temperaturecooled
  16. customThe crystals formed
  17. filtrationwere collected by filtration
  18. customdried under reduced pressure

Sources & evidence

ORD record
ord-153fffa770894a1fb0b2a21f4fbf59b0
Source dataset
uspto-grants-1999_11
Patent number
US05981559

Reaction notes

Loading…