Trimethylamine → N-(2,4,4-trimethylcyclopenten-1-yl)-N-methyl-alpha-chloroacetamide
Reaction equation
CC1(C)CC(C)CC1=O.CC1CC(C)(C)CC1=O.S([O-])([O-])(=O)=O.[NH4+].[NH4+].CN.ClCC(Cl)=O.CN(C)C.[CH3:37][C:38]1([CH3:50])[CH2:42][CH:41]([CH3:43])[C:40]([N:44]([CH3:49])[C:45](=[O:48])[CH2:46][Cl:47])=[CH:39]1.CC1CC(C)(C)C(N(C)C(=O)CCl)=C1>C1C=CC=CC=1>[CH3:43][C:41]1[CH2:42][C:38]([CH3:37])([CH3:50])[CH2:39][C:40]=1[N:44]([CH3:49])[C:45](=[O:48])[CH2:46][Cl:47]Participants
Reactant 8
HCID 1146Trimethylamine
HCID 6329Methylamine
HCID 6577Chloroacetyl chloride
HCID 1073242,4,4-Trimethylcyclopentanone
HCID 1196322,2,4-Trimethylcyclopentanone
HCID 6097028Ammonium Sulfate
HCID 20548521N-(3,5,5-trimethylcyclopenten-1-yl)-N-methyl-alpha-chloroacetamide
HCID 20548522N-(3,3,5-trimethylcyclopenten-1-yl)-N-methyl-alpha-chloroacetamideProduct 1
Reagents, catalysts & solvents 1
Procedure
By the same procedure as in Example 1 using a mixture comprising 2,2,4-trimethylcyclopentanone and 2,4,4-trimethylcyclopentanone (about 1:1) (25.2 parts by weight) in 150 milliliters of benzene, one part by weight of ammonium sulfate and 6.2 parts by weight of methylamine, further reacted with 22.6 parts by weight of chloroacetyl chloride and 24.6 parts by weight of trimethylamine, a mixture of isomers consisting of N-(3,3,5-trimethylcyclopenten-1-yl)-N-methyl-α-chloroacetamide, N-(3,5,5-trimethylcyclopenten-1-yl)-N-methyl-α-chloroacetamide, and N-(2,4,4-trimethylcyclopenten-1-yl)-N-methyl-α-chloroacetamide was obtained. The yield of partially crystalline dark brown product amounted to 33 parts by weight. The molecular weight was determined to be 198 (215). The content of organically combined chlorine was 17.5% (16.5%). The nitrogen content was 6.3% (6.5%).
Workup
- additiona mixture of isomers
Sources & evidence
- ORD record
- ord-92838ca964e34dc0a04d5dabd5b80fcc
- Source dataset
- uspto-grants-1982_03
- Patent number
- US04319918
Reaction notes
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