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

HRID 409420Notes

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]

Participants

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

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

Sources & evidence

ORD record: ord-fe1bd3ffd0aa445a80ed67751eae6679
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759388B2

Reaction notes

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