Thionyl Chloride → HCID 86737729, compound

HRID 2286596Notes

Reaction equation

HRID 2286596 reaction equation
O[CH2:2][CH2:3][NH:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]([OH:21])([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])=[CH:7][C:6]=1[CH3:22].O=S(Cl)[Cl:25]>C(Cl)(Cl)Cl.CCCCCC>[ClH:25].[Cl:25][CH2:2][CH2:3][NH:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]([OH:21])([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])=[CH:7][C:6]=1[CH3:22]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 15572225HCID 15572225, compound

Product 1

HCID 86737729HCID 86737729, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8058HexaneSolvent

Procedure

Dissolve the N-(2-hydroxyethyl)-2,6-dimethyl-4-(hexafluoro-2-hydroxy-2-propyl)aniline (40.0 g, 0.12 mol) in 300 ml CHCl3. Add a solution of SOCl2 (59.5 g, 0.50) in 100 ml CHCl3. Reflux 16 hours, allow to cool, and dilute with an equal volume of hexane. Filter to give solid, m.p. 190°-196° C. (dec.), N-(2-chloroethyl)-2,6-dimethyl-4-(hexafluoro-2-hydroxy-2-propyl)aniline hydrochloride. The corresponding free base has m.p. 101°-104° C.

Workup

  1. temperatureReflux 16 hours
  2. temperatureto cool
  3. filtrationFilter

Sources & evidence

ORD record
ord-6767370a2aae4877a75e353693b4981d
Source dataset
uspto-grants-1981_05
Patent number
US04267193

Reaction notes

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