1,2-Dichloroethane → Methyl 4-(2-(dimethylamino)-2-(thiophen-3-yl)acetamido)benzoate

HRID 509240Notes

Reaction equation

HRID 509240 reaction equation
[CH3:1][N:2]([CH3:12])[CH:3]([C:7]1[CH:11]=[CH:10][S:9][CH:8]=1)[C:4]([OH:6])=O.[CH2:13](Cl)CCl.[NH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([O-:24])=[O:23])=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[CH3:12][N:2]([CH3:1])[CH:3]([C:7]1[CH:11]=[CH:10][S:9][CH:8]=1)[C:4]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([O:24][CH3:13])=[O:23])=[CH:20][CH:19]=1)=[O:6]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 48764-AminobenzoateHCID 516892Sodium BicarbonateHCID 438031702-(Dimethylamino)-2-(thiophen-3-yl)acetic acid

Product 1

HCID 59161754Methyl 4-(2-(dimethylamino)-2-(thiophen-3-yl)acetamido)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 2-(dimethylamino)-2-(thiophen-3-yl)acetic acid in pyridine was added EDC, DMAP and 4-aminobenzoate and the solution was stirred for 10 hours at room temperature. The mixture was poured into NaHCO3 (sat) and extracted with EtOAc. The extracts were dried (MgSO4), filtered and evaporated. Column chromatography (SiO2, 0-100% EtOAc/Hex) gave pure methyl 4-(2-(dimethylamino)-2-(thiophen-3-yl)acetamido)benzoate (E114).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extracts were dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-c2244893f0df46c887672e1ed01468aa
Source dataset
uspto-grants-2015_08
Patent number
US09096569B2

Reaction notes

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