1,2-Dichloroethane → 4-(2-(Dimethylamino)-2-(thiophen-3-yl)acetamido)-2-methylbenzamide

HRID 1690265Notes

Reaction equation

HRID 1690265 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.C(Cl)CCl.[NH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH2:24])=[O:23])=[C:20]([CH3:27])[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]([NH2:24])=[O:23])=[C:20]([CH3:27])[CH:19]=1)=[O:6]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 516892Sodium BicarbonateHCID 230682064-Amino-2-methylbenzamideHCID 438031702-(Dimethylamino)-2-(thiophen-3-yl)acetic acid

Product 1

HCID 591617364-(2-(Dimethylamino)-2-(thiophen-3-yl)acetamido)-2-methylbenzamide

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-amino-2-methylbenzamide (E112) 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 4-(2-(dimethylamino)-2-(thiophen-3-yl)acetamido)-2-methylbenzamide (E113).

Workup

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

Sources & evidence

ORD record
ord-05ce8c57277449b1be1512c3989ab902
Source dataset
uspto-grants-2012_04
Patent number
US08153656B2

Reaction notes

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