Thionyl Chloride → HCID 20360379, compound

HRID 2082676Notes

Reaction equation

HRID 2082676 reaction equation
[C:1]1([CH:7]([NH:18][CH2:19][CH2:20]O)[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:24])=O>CC1C=CC=CC=1>[ClH:24].[Cl:24][CH2:20][CH2:19][NH:18][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20360357HCID 20360357, compound

Product 1

HCID 20360379HCID 20360379, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

To a stirred and cooled (5°-10° C) mixture of 60 parts of 2-[{phenyl[3-(trifluoromethyl)phenyl]methyl}amino]-ethanol and 540 parts of methylbenzene are added dropwise 40 parts of sulfinyl chloride. Upon completion, stirring is continued first till room temperature is reached and further overnight at reflux temperature. The reaction mixture is concentrated to one third its volume. After cooling to 10° C, the solid product is filtered off, washed with 2,2'-oxybispropane and dried in vacuo at 75° C, yielding 28.5 parts (40%) of N-(2-chloroethyl)-α-phenyl-3-(trifluoromethyl)benzenemethanamine hydrochloride; mp. 187° C.

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. customis continued first till room temperature
  4. temperatureat reflux temperature
  5. concentrationThe reaction mixture is concentrated to one third its volume
  6. filtrationthe solid product is filtered off
  7. washwashed with 2,2'-oxybispropane
  8. customdried in vacuo at 75° C

Sources & evidence

ORD record
ord-dd63033918274148833049e4b202a1d6
Source dataset
uspto-grants-1978_04
Patent number
US04082755

Reaction notes

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