Dichloromethane → 61551-70-0

HRID 428357Notes

Reaction equation

HRID 428357 reaction equation
S(Cl)([Cl:3])=O.[N:5]([C:16]([CH3:24])([CH3:23])[C:17]([NH:19][CH2:20]CO)=[O:18])=[N:6][C:7]([CH3:15])([CH3:14])[C:8]([NH:10][CH2:11][CH2:12]O)=[O:9].C1CCCCC1.Cl[CH2:32][Cl:33]>>[N:5]([C:16]([CH3:24])([CH3:23])[C:17]([NH:19][CH2:20][CH2:32][Cl:33])=[O:18])=[N:6][C:7]([CH3:15])([CH3:14])[C:8]([NH:10][CH2:11][CH2:12][Cl:3])=[O:9]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8078CyclohexaneHCID 24386Thionyl ChlorideHCID 381605Propanamide, 2,2'-(1,2-diazenediyl)bis[N-(2-hydroxyethyl)-2-methyl-

Product 1

HCID 1090346461551-70-0

Procedure

Thionyl chloride (50 ml) was added at 0° C. under an atmosphere of inert gas (argon) to a suspension of 2,2′-azobis[2-methyl-N-(2-hydroxyethyl)propionamide] (38.3 g) in dichloromethane (180 ml) over a period of 30 minutes. The mixture was stirred at room temperature for 18 h, and the precipitate which formed was filtered off, suspended in 100 ml of water and stirred for 5 min. The solid was separated off and dried under reduced pressure at room temperature for 24 h (8.9 g). Further product was isolated from the organic phase of the reaction mixture by adding cyclohexane (250 ml) and cooling to 0° C. The precipitate which formed was filtered off, and worked up and isolated as described above (10.8 g). Finally, the remaining organic filtrate was concentrated to low volume. The precipitate which formed was subjected to the procedure described above (7.6 g).

Workup

  1. customthe precipitate which formed
  2. filtrationwas filtered off
  3. stirringstirred for 5 min
  4. customThe solid was separated off
  5. customdried under reduced pressure at room temperature for 24 h (8.9 g)
  6. customFurther product was isolated from the organic phase of the reaction mixture
  7. temperaturecooling to 0° C
  8. customThe precipitate which formed
  9. filtrationwas filtered off
  10. customisolated
  11. concentrationFinally, the remaining organic filtrate was concentrated to low volume
  12. customThe precipitate which formed

Sources & evidence

ORD record
ord-13902c948ff8403baf0225e3ded0adc0
Source dataset
uspto-grants-2001_11
Patent number
US06313275B1

Reaction notes

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