Diphenyl Ether → HCID 10443297, compound

HRID 651606Notes

Reaction equation

HRID 651606 reaction equation
C([N:5]([CH2:10]CCC)CCCC)CCC.[C:14]([NH:17][C:18]1[CH:19]=[C:20]([CH:25]=[CH:26]C(N=[N+]=[N-])=O)[CH:21]=[CH:22][C:23]=1[CH3:24])(=[O:16])[CH3:15].CCCCCC.C1([O:44]C2C=CC=CC=2)C=CC=CC=1>>[CH3:24][C:23]1[CH:22]=[C:21]2[C:20]([CH:25]=[CH:26][NH:5][C:10]2=[O:44])=[CH:19][C:18]=1[NH:17][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 4

HCID 7583Diphenyl Ether2×HCID 7622TributylamineHCID 8058HexaneHCID 54054125HCID 54054125, compound

Product 1

HCID 10443297HCID 10443297, compound

Procedure

To a solution of diphenyl ether (250 mL) and tributylamine (11.9 mL, 49.9 mmol) at 220-240° C. is added a slurry of 3-(3-acetylamino-4-methyl-phenyl)-acryloyl azide (12.2 g, 49.9 mmol) in diphenyl ether. After 2 hours, the yellow solution is cooled to room temperature and poured over hexane (800 mL). A brown solid precipitates out and the title product (3.56 g, 16.5 mmol) is obtained as a light yellow solid by recrystallization from DMF/MeOH.

Sources & evidence

ORD record
ord-4aec73027aba41e69e5380d80868ce35
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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