Glycol monoethyl ether → HCID 101835019, compound

HRID 1164241Notes

Reaction equation

HRID 1164241 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([O-:14])(=[O:13])=[O:12].[Na+:15].[Na].[H-].[Na+].[CH3:19][CH2:20][O:21][CH2:22][CH2:23][OH:24]>>[CH2:20]([O:21][CH2:22][CH2:23][O:24][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([O-:14])(=[O:13])=[O:12])[CH3:19].[Na+:15]

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 24758Sodium hydrideHCID 70350Benzenesulfonic acid, 2-chloro-5-nitro-, sodium salt (1:1)HCID 5360545Sodium

Product 1

HCID 101835019HCID 101835019, compound

Procedure

55 g of sodium 2-chloro-5-nitrobenzenesulfonate was added to a sodium 2-ethoxyethylate solution prepared by adding 7.3 g of sodium hydride (14.6 g in the form of a 50% liquid paraffin suspension) to 300 ml of ethyl cellosolve. This reaction mixture was stirred for 30 minutes while maintaining the temperature at 80° to 85° C. After completion of the reaction, insolubles were filtered off, and 150 ml of ethyl cellosolve was distilled out of the filtrate. 300 ml of isopropyl alcohol was added to the concentrate and cooled with ice. Crystals thus formed were collected by filtration, washed with 100 ml of isopropyl alcohol, and air-dried. Yield: 33 g; m.p. above 250° C.

Workup

  1. customprepared
  2. temperaturewhile maintaining the temperature at 80° to 85° C
  3. customAfter completion of the reaction, insolubles
  4. filtrationwere filtered off
  5. distillation150 ml of ethyl cellosolve was distilled out of the filtrate
  6. addition300 ml of isopropyl alcohol was added to the
  7. concentrationconcentrate
  8. temperaturecooled with ice
  9. customCrystals thus formed
  10. filtrationwere collected by filtration
  11. washwashed with 100 ml of isopropyl alcohol
  12. customair-dried

Sources & evidence

ORD record
ord-ae829118816a4f3cb0b05d84329b93e1
Source dataset
uspto-grants-1983_01
Patent number
US04368251

Reaction notes

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