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Formamide → 4-(2-(Dimethylamino)-2-(thiophen-3-yl)acetamido)benzamide

HRID 509241
Notes
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Reaction equation

HRID 509241 reaction equation
[CH3:1][N:2]([CH3:22])[CH:3]([C:17]1[CH:21]=[CH:20][S:19][CH:18]=1)[C:4]([NH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](OC)=[O:12])=[CH:9][CH:8]=1)=[O:5].C([NH2:25])=O.C[O-].[Na+]>CN(C=O)C>[CH3:1][N:2]([CH3:22])[CH:3]([C:17]1[CH:21]=[CH:20][S:19][CH:18]=1)[C:4]([NH:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([NH2:25])=[O:12])=[CH:9][CH:8]=1)=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 713FormamideHCID 10942334Sodium MethoxideHCID 59161754Methyl 4-(2-(dimethylamino)-2-(thiophen-3-yl)acetamido)benzoate

Product 1

HCID 461846044-(2-(Dimethylamino)-2-(thiophen-3-yl)acetamido)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 4-(2-(dimethylamino)-2-(thiophen-3-yl)acetamido)benzoate (E114) and formamide dissolved in DMF under Ar were heated to 100° C. The NaOMe was then added and the reaction heated for 2 hours. The reaction was partitioned between EtOAc and water. The aqueous layer was 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)benzamide (E115).

Workup

  1. temperaturethe reaction heated for 2 hours
  2. customThe reaction was partitioned between EtOAc and water
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialThe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-106b258c557e4dbc9e0fccd8823e24d4
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09096569B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes