Dimethylformamide → HCID 59571733, compound

HRID 2194306Notes

Reaction equation

HRID 2194306 reaction equation
[H-].[Na+].CN(C)C=O.[CH2:8]([O:11][C:12]1[C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][C:16]=2[CH:15]=[CH:14][CH:13]=1)[CH:9]=[CH2:10].Cl[CH2:26][C:27]1[CH:46]=[CH:45][C:30]([O:31][CH2:32][C:33]2[N:34]=[C:35]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[O:36][C:37]=2[CH3:38])=[C:29]([O:47][CH3:48])[CH:28]=1>C(OCC)(=O)C.CCCCCC>[CH3:38][C:37]1[O:36][C:35]([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[N:34][C:33]=1[CH2:32][O:31][C:30]1[CH:45]=[CH:46][C:27]([CH2:26][N:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([O:11][CH2:8][CH:9]=[CH2:10])[C:24]=3[C:23]3[C:18]2=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:28][C:29]=1[O:47][CH3:48]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 223446094-(4-Chloromethyl-2-methoxyphenoxymethyl)-5-methyl-2-phenyloxazoleHCID 595717514-(2-Propen-1-yloxy)-9H-carbazole

Product 1

HCID 59571733HCID 59571733, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6.05 g of sodium hydride (60%) was added to N,N-dimethylformamide (170 mL) solution of 35 g of 4-(allyloxy)-9H-carbazole while being cooled in an ice bath, and stirred at room temperature for 1 hour. Thereafter, 49.4 g of 4-((4-(chloromethyl)-2-methoxyphenoxy)methyl)-5-methyl-2-phenyloxazole was added thereto, and stirred for 1 hour. The reaction mixture was diluted with mixture of ethyl acetate:n-hexane=1:1 (340 mL), poured into ice water (680 mL), and stirred for 1 hour. The crystalline precipitate was isolated by filtration, and washed with mixture of ethyl acetate:n-hexane=1:1. The crystalline precipitate was dried under reduced pressure, and 55.4 g the subject compound was prepared as pale yellow crystal.

Workup

  1. temperaturewhile being cooled in an ice bath
  2. stirringstirred for 1 hour
  3. stirringstirred for 1 hour
  4. customThe crystalline precipitate was isolated by filtration
  5. washwashed with mixture of ethyl acetate
  6. dry with materialThe crystalline precipitate was dried under reduced pressure, and 55.4 g the subject compound
  7. customwas prepared as pale yellow crystal

Sources & evidence

ORD record
ord-152712060b5e4a6684cef2a4e291390a
Source dataset
uspto-grants-2012_12
Patent number
US08329913B2

Reaction notes

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