Ethyl 2-chloro-2-ethoxyacetate → HCID 20386798, compound

HRID 46672

Reaction equation

HRID 46672 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5][CH2:6][CH2:7][C:8]1[S:9][CH:10]=[CH:11][CH:12]=1.Cl[CH:18](OCC)[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O>[ClH:1].[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][C:8]2[S:9][CH:10]=[CH:11][C:12]=2[CH:18]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 2724873Ethyl 2-chloro-2-ethoxyacetateHCID 6454012N-((2-chlorophenyl)methyl)thiophene-3-ethylamine

Product 1

HCID 20386798HCID 20386798, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a three-necked 250 ml flask are added 25.1 g (0.1 M) N- (2-chloro-benzyl)-2-(2-thienyl)ethylamine dissolved in 30 ml dimethylformamide. Ethyl 2-chloro-2-ethoxy-acetate (18.3 g; 0.11 M) is then added over 6 minutes, and the resulting material is heated at 80° C. for 4 hours after which the desired product begins to precipitate out. After cooling of the medium, the product is filtered off and recrystallized from 3×20 ml acetone, to give 20.5 g 5-(2-chloro-benzyl)-4-ethoxy-carbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (Yield: 55%).

Sources & evidence

ORD record
ord-ddc8b318bdba4eab8f2bb8a47c74d1a0
Source dataset
uspto-grants-1979_11
Patent number
US04174448

Linked notes

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