N,N-Dimethylaniline → 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
Reaction equation
[OH:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5].CN(C)C1C=CC=CC=1.Cl[C:22]([O:24]C(Cl)(Cl)Cl)=[O:23].ClC(ON=[C:34]([C:37]1[CH:42]=CC=C[CH:38]=1)C#N)=O>CC(C)=O.C1C=CC=CC=1.N1C=CC=CC=1.C(O)(C)(C)C>[C:37]([O:24][C:22]([O:1][N:2]=[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:4]#[N:5])=[O:23])([CH3:34])([CH3:38])[CH3:42]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
A solution of 2-hydroxyimino-2-phenylacetonitrile (14.6 g.) and dimethylaniline (13.2 g.) in a mixture of acetone (5 ml.) and benzene (80 ml.) was added dropwise to a solution of trichloromethyl chloroformate (phosgene dimer) (6.7 ml.) in benzene (30 ml.) under ice-cooling. The mixture was stirred for 6 hours at the same temperature and allowed to stand overnight. A mixture of tert-butyl alcohol (11.1 g.), pyridine (16.0 ml.) and benzene (20 ml.) was added dropwise, under ice-cooling, to the resultant mixture containing 2-chlorocarbonyloxyimino-2-phenyl-acetonitrile. The mixture was stirred for 7 hours at room temperature and allowed to stand overnight. The reaction mixture was treated as described in the above Examples 2(A) to 2(F) to give 2-tert-butoxycarbonyloxyimino-2-phenylacetonitrile (17.0 g.), mp 84° to 86° C.
Workup
- temperaturecooling
- waitto stand overnight
- additionwas added dropwise, under ice-
- stirringThe mixture was stirred for 7 hours at room temperature
- waitto stand overnight
- additionThe reaction mixture was treated
Sources & evidence
- ORD record
- ord-d8f30aea2e2f4af9bcd1c989de5541cf
- Source dataset
- uspto-grants-1978_04
- Patent number
- US04083848
Reaction notes
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