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

HRID 409419Notes

Reaction equation

HRID 409419 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-dbe87cc152234c83b819ec7f83ab6ec2
Source dataset
uspto-grants-2014_06
Patent number
US08759388B2

Reaction notes

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