Dimethylformamide → HCID 18707475, compound
Reaction equation
P(Cl)(Cl)(Cl)=O.CN([CH:9]=[O:10])C.[C:11]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:24]3[C:19]2=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:13][CH:12]=1>O>[C:31]1([C:11]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[C:19]4[CH:20]=[CH:21][C:22]([CH:9]=[O:10])=[CH:23][C:24]=4[C:25]4[C:30]3=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:13][CH:12]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Under a atmosphere of nitrogen at 0° C. phosphorous oxychloride (3.0 ml, 33 mmol) was added dropwise to N,N'-dimethylformamide (1.2 ml, 15.8 mmol). After the addition was complete, the mixture was stirred at 0° C. for 1 h and heated to 45° C. At 45° C. the above carbazole (5.00 g, 15 mmol) was added during 15 minutes. The solid reaction mixture was then heated at 95° C. for 16 h. To the cooled reaction mixture water (125 ml) was added and the mixture was stirred vigorously at room temperature for 4 h. The solid formed was filtered off, washed with water and dried in vacuo at 50° C. affording almost quantitatively 9-(4-phenylbenzyl)-9H-carbazole-3-carboxaldehyde as a solid.
Workup
- additionAfter the addition
- temperatureheated to 45° C
- customThe solid reaction mixture
- temperaturewas then heated at 95° C. for 16 h
- additionwas added
- stirringthe mixture was stirred vigorously at room temperature for 4 h
- customThe solid formed
- filtrationwas filtered off
- washwashed with water
- customdried in vacuo at 50° C.
Sources & evidence
- ORD record
- ord-cd0bf047fda84add843120978d954950
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06080770
Reaction notes
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