Aniline → HCID 19047174, compound
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[CH2:10][CH:11]([C:16]([F:19])([F:18])[F:17])[CH2:12][C:13]([OH:15])=O)=[CH:4][CH:3]=1.NC1C=CC=CC=1.C1(=O)OC(=O)CCC1.C(Cl)(=O)C>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9](=[O:20])[CH2:10][CH:11]([C:16]([F:19])([F:18])[F:17])[CH2:12][C:13]2=[O:15])=[CH:4][CH:3]=1Participants
5
Procedure
Into a 50 ml 1-necked, round-bottomed flask containing a stir bar were placed 2.50 g (7.96 mmol) N-(4'-bromophenyl)-3-(trifluoromethyl)glutaramic acid (prepared as described in Example 1 from the appropriate aniline and glutaric anhydride) and acetyl chloride (15 ml). The mixture was heated to reflux for 6 hours resulting in a clear, light grey solution. The acetyl chloride was removed via atmospheric distillation through a short path distillation head. The resulting light grey crystalline solid was triturated with hexanes, filtered and washed with hexanes to yield an off-white crystalline solid which was dried in vacuo at 50° C. to yield 2.10 g (89% yield) of product, m.p. 163°-4° C.
Workup
- additionInto a 50 ml 1-necked, round-bottomed flask containing a stir bar
- customprepared
- temperatureThe mixture was heated
- temperatureto reflux for 6 hours
- customresulting in a clear, light grey solution
- customThe acetyl chloride was removed via atmospheric distillation through a short path distillation head
- customThe resulting light grey crystalline solid was triturated with hexanes
- filtrationfiltered
- washwashed with hexanes
- customto yield an off-white crystalline solid which
- customwas dried in vacuo at 50° C.
Sources & evidence
- ORD record
- ord-89739ceaf7a446cc8e8220a4e90833ea
- Source dataset
- uspto-grants-1997_05
- Patent number
- US05631209
Reaction notes
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