Dimethylformamide → HCID 9951655, compound
Reaction equation
S(O[CH2:12][CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[O:14]1)(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].[C:29]1([N:35]2[C:39]3([CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)[C:38](=[O:45])[NH:37][CH2:36]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.CN(C)C=O>>[O:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:21][CH2:22][CH:13]1[CH2:12][N:42]1[CH2:41][CH2:40][C:39]2([N:35]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:36][NH:37][C:38]2=[O:45])[CH2:44][CH2:43]1Participants
5
Procedure
The mixture from 31.8 g (0.1 mol) of 2-tosyloxymethyl-chroman, 7.1 g (0.07 mol) of anhydrous sodium carbonate and 23.1 g (0.1 mol) of 1-phenyl-1,3,8-triazaspiro[4.5]-decan-4-one in 240 mol of anhydrous dimethylformamide (DMF) is stirred at 110° C. for 6 h and then poured onto ice (500 g). After extracting with ethyl acetate (5×100 ml), washing the organic extracts with water, drying over anhydrous sodium sulphate and evaporating the organic phase in a water jet vacuum, 65.7 g of solvent-containing crystalline crude product are obtained which, recrystallised twice from ethyl acetate, yields 20.6 g of the title compound of m.p. 192-193.5° C.
Workup
- additionpoured onto ice (500 g)
- extractionAfter extracting with ethyl acetate (5×100 ml)
- washwashing the organic extracts with water
- dry with materialdrying over anhydrous sodium sulphate
- customevaporating the organic phase in a water jet vacuum, 65.7 g of solvent-containing crystalline crude product
- customare obtained which
- customrecrystallised twice from ethyl acetate
Sources & evidence
- ORD record
- ord-e7d1e91d926f40b097cf4eef10b15e67
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06060482
Reaction notes
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