tert-Butoxy bis(dimethylamino)methane → 7-[(Dimethylamino)methylene]-4,5,6,7-tetrahydro-4-4-nitrobenzyl-8H-thieno[3,2-b]azepin-8-one
Reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]3[S:18][CH:19]=[CH:20][C:11]2=3)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(O[CH:28](N(C)C)[N:29]([CH3:31])[CH3:30])(C)(C)C>>[CH3:28][N:29]([CH:31]=[C:14]1[CH2:15][CH2:16][N:10]([CH2:8][C:7]2[CH:21]=[CH:22][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:11]2[CH:20]=[CH:19][S:18][C:12]=2[C:13]1=[O:17])[CH3:30]Participants
3
Procedure
A mixture of 3.2 g of 4,5,6,7-tetrahydro-4-(4-nitrobenzoyl)-8H-thieno[3,2-b]azepin-8-one and 32 ml of tert-butoxybis(dimethylamino)methane is heated on a steam bath for 3.5 hours. The reaction mixture is allowed to stand for 48 hours. The reaction mixture is evaporated in vacuo and the concentrate is dissolved in 150 ml of methylene chloride and filtered through hydrous magnesium silicate two times. The volatiles are evaporated in vacuo to a residue which is dissolved in 25 ml of ethyl acetate and filtered. The filtrate is cooled to give 3.2 g of the desired product as a light orange solid, m.p. 214°-216° C.
Workup
- temperatureis heated on a steam bath for 3.5 hours
- customThe reaction mixture is evaporated in vacuo
- dissolutionthe concentrate is dissolved in 150 ml of methylene chloride
- filtrationfiltered through hydrous magnesium silicate two times
- customThe volatiles are evaporated in vacuo to a residue which
- dissolutionis dissolved in 25 ml of ethyl acetate
- filtrationfiltered
- temperatureThe filtrate is cooled
Sources & evidence
- ORD record
- ord-ae1fc3543e1749939e12a883eca6fb18
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05719278
Reaction notes
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