Chloroacetic Acid → 2-Chloro-N-[2-(dimethylamino)ethyl]acetamide
Reaction equation
[Cl:1][CH2:2][C:3]([OH:5])=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:48][N:49]([CH3:53])[CH2:50][CH2:51][NH2:52]>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:52][CH2:51][CH2:50][N:49]([CH3:53])[CH3:48])=[O:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of 2-chloroacetic acid (214 mg, 2.27 mmol), PyBOP® (1.18, 2.27 mmol), DIEA (1.18 mL, 6.81 mmol) in CH2Cl2 (1 mL) was stirred at RT for 10-15 minutes. This solution of activated acid was added to a suspension of N1,N1-dimethylethane-1,2-diamine (249 μL, 2.27 mmol) and CH2Cl2 (4 mL). The reaction mixture was stirred at RT for 1.5 h. Diluted with more CH2Cl2 and extracted with H2O (3×). Organic layer was dried under Na2SO4 and concentrated in vacuo to give the desired product 2-chloro-N-(2-(dimethylamino)ethyl)acetamide.
Workup
- stirringThe reaction mixture was stirred at RT for 1.5 h
- extractionextracted with H2O (3×)
- customOrganic layer was dried under Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c6fff763172447178ab474d2498939b9
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08357693B2
Reaction notes
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