Water → N-methoxy-N-methylthiophene-3-carboxamide

HRID 875224Notes

Reaction equation

HRID 875224 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6](Cl)=[O:7])=[CH:2]1.Cl.[CH3:10][NH:11][O:12][CH3:13].C(N(CC)CC)C.O>ClCCl>[CH3:13][O:12][N:11]([CH3:10])[C:6]([C:3]1[CH:4]=[CH:5][S:1][CH:2]=1)=[O:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27763773-Thenoyl chloride

Product 1

HCID 22489894N-methoxy-N-methylthiophene-3-carboxamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of this crude thiophene-3-carbonyl chloride (97.7 g, 666 mmol) and N,O-dimethylhydroxylamine hydrochloride (71.5 g, 733 mmol) in dichloromethane (600 mL) at 0° C. was added dropwise triethylamine (186 mL, 1.33 mol). After stirring at room temperature for 3 h, the reaction mixture was poured into water (2 L), the layers were separated and the aqueous layer extracted with dichloromethane (2×200 mL). The combined organic layers were washed with water (200 mL), then dried over MgSO4 and concentrated in vacuo to afford N-methoxy-N-methylthiophene-3-carboxamide [102.2 g, yield 90%; HPLC/MS: m/z=172 (M+H); log P(HCOOH)=1.30].

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer extracted with dichloromethane (2×200 mL)
  3. washThe combined organic layers were washed with water (200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2dcc14ae362c46b4a7d71645f330eb0d
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

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