Acetic Anhydride → 4,4'-Methylenebis[2,6-diethylaniline]
Reaction equation
FC(F)(F)[C:3]([C:19]1[CH:20]=C2[C:25](=[CH:26][CH:27]=1)[C:24](=O)OC2=O)([C:8]1[CH:9]=C2[C:14](=[CH:15][CH:16]=1)[C:13](=O)OC2=O)C(F)(F)F.[C:32](OC(=O)C)(=O)[CH3:33].C([N:41]([CH2:44][CH3:45])CC)C.C[N:47]1[CH2:51][CH2:50][CH2:49][C:48]1=O>>[CH2:3]([C:8]1[CH:16]=[C:15]([CH2:14][CH3:13])[C:51]([NH2:47])=[C:50]([CH2:49][CH3:48])[CH:9]=1)[C:19]1[CH:20]=[C:45]([CH2:32][CH3:33])[C:44]([NH2:41])=[C:26]([CH2:25][CH3:24])[CH:27]=1Participants
Procedure
in N-methylpyrrolidone (350 ml) was added 5,5'[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]-bis-1,3-isobenzofurandione (67.27 g, 0.1515 mol) under an inert atmosphere at room temperature. The resulting viscous orange solution was stirred overnight at room temperature. A solution of acetic anhydride (61.25 ml, 0.60 mol) and triethylamine (60.71 ml, 0.60 mol) was added with rapid stirring at room temperature. After stirring for 3 hours, the solution was diluted with additional N-methylpyrrolidone and precipitated in water. The resulting solid was collected and washed twice with water, washed twice with methanol, and allowed to air dry. The solid was further dried in a vacuum oven at 20 inches (0.51 m) mercury and 100° C. for 15 hours and at 245° C. for 4 hours to yield 99.4 g product.
Workup
- stirringwith rapid stirring at room temperature
- stirringAfter stirring for 3 hours
- customprecipitated in water
- customThe resulting solid was collected
- washwashed twice with water
- washwashed twice with methanol
- customto air dry
- dry with materialThe solid was further dried in a vacuum oven at 20 inches (0.51 m) mercury and 100° C. for 15 hours and at 245° C. for 4 hours
Sources & evidence
- ORD record
- ord-4143b0689d6d4b6da2afafab79203e68
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04932983
Reaction notes
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