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

HRID 2097234Notes

Reaction equation

HRID 2097234 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-ad51eaac0a474bb58b85432d06fa3b45
Source dataset
uspto-grants-2013_05
Patent number
US08450344B2

Reaction notes

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