1-Chloro-4-(chloromethyl)benzene → HCID 12361851, compound

HRID 128099Notes

Reaction equation

HRID 128099 reaction equation
C(OC1CC2C3[C:15](=CC=CC=3)[NH:14][C:13]=2CC1)(=O)C1C=CC=CC=1.[H-].[Na+].ClC1C=CC(CCl)=CC=1.C(O[CH:43]1[CH2:55][C:54]2[C:53]3[C:48](=[CH:49][CH:50]=[CH:51][CH:52]=3)[N:47]([CH2:56][C:57]3[CH:62]=[CH:61][C:60]([Cl:63])=[CH:59][CH:58]=3)[C:46]=2[CH2:45][CH2:44]1)(=O)C1C=CC=CC=1>O.CN(C)C=O>[Cl:63][C:60]1[CH:61]=[CH:62][C:57]([CH2:56][N:47]2[C:46]3[CH2:45][CH2:44][CH:43]([N:14]([CH3:15])[CH3:13])[CH2:55][C:54]=3[C:53]3[C:48]2=[CH:49][CH:50]=[CH:51][CH:52]=3)=[CH:58][CH:59]=1

Participants

7

Reactant 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 12891847HCID 12891847, compoundHCID 23470342HCID 23470342, compound

Product 1

HCID 12361851HCID 12361851, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

A mixture of 29.1 g. of 3-benzoyloxy-1,2,3,4-tetrahydrocarbazole and 4.3 g. of sodium hydride (56% in mineral oil) in 200 ml. of dimethylformamide was heated on a steam bath and 16.1 g. of p-chlorobenzyl chloride in 30 ml. of dimethylformamide was added dropwise. The reaction mixture was heated two hours, cooled, and diluted with water. The resulting oil was washed with water and crystallized from isopropyl alcohol to give 12.7 g. of 3-benzoyloxy-9-(p-chlorobenzyl)-1,2,3,4-tetrahydrocarbazole, m.p. 150°-152° C.

Workup

  1. additionA mixture of 29.1 g
  2. temperatureThe reaction mixture was heated two hours
  3. temperaturecooled
  4. washThe resulting oil was washed with water
  5. customcrystallized from isopropyl alcohol
  6. customto give 12.7 g

Sources & evidence

ORD record
ord-ad9130a5b09e44ba8972c66bf6cc0c17
Source dataset
uspto-grants-1981_03
Patent number
US04257952

Reaction notes

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