Thionyl Chloride → HCID 20095065, compound

HRID 1770151Notes

Reaction equation

HRID 1770151 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([OH:20])=O)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].S(Cl)([Cl:23])=O>CN(C=O)C>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([Cl:23])=[O:20])[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 20095034HCID 20095034, compound

Product 1

HCID 20095065HCID 20095065, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

In a 50 ml-round bottomed flask, 5.00 g (18.2 mM) of 2-octylindan-5-carboxylic acid was placed and 7.0 ml of thionyl chloride and one drop of N,N'-dimethylformamide (DMF) were added thereto, followed by heat-refluxing for 30 minute. An excessive thionyl chloride was distilled off under reduced pressure from the above mixture to obtain 2-octylindan-5-carbonyl chloride. A solution of the above-obtained 2-octylindan-5-carbonyl chloride in 50 ml of THF was gradually added dropwise to 45 ml of 30%-ammonia water which had been cooled to about 0° C. on an ice-common salt bath under stirring. After the addition, the resultant mixture was stirred for 4.5 hours at room temperature. After the reaction, 300 ml of water was added to the reaction mixture to precipitate a crystal. The crystal was recovered by filtration and successively washed with water and methanol to obtain 4.59 g of 2-octyl-5-carbamoylindan (Yield: 92.1%).

Workup

  1. temperatureby heat-refluxing for 30 minute
  2. distillationAn excessive thionyl chloride was distilled off under reduced pressure from the above mixture

Sources & evidence

ORD record
ord-d30e1571a77040d392b6d7da50f0b251
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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