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

HRID 509239
Notes
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Reaction equation

HRID 509239 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 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-5bda8d283f1442c7a18001098f37e5fb
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096569B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes