Propionic Acid → Ethyl 4-methyl-2-(N'-methylureido)thiophene-3-carboxylate

HRID 502541

反応式

HRID 502541 の反応式
[C:1]([OH:5])(=O)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH2:23]([N:25](CC)CC)C.[NH2:30][C:31]1[S:32][CH:33]=[C:34]([CH3:41])[C:35]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37]>C1(C)C=CC=CC=1>[CH3:41][C:34]1[C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:31]([NH:30][C:1]([NH:25][CH3:23])=[O:5])[S:32][CH:33]=1

参加物

6

反応物 4

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylate

生成物 1

HCID 15085569Ethyl 4-methyl-2-(N'-methylureido)thiophene-3-carboxylate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of propionic acid (3.8 ml, 50.64 mmol), diphenylphosphoryl azide (10.9 ml, 50.64 mmol), and triethylamine (7.1 ml, 50.64 mmol) in toluene (30 ml) was refluxed for 1 hour. After cooling to room temperature, ethyl 2-amino-4-methylthiophene-3-carboxylate (3.13 g, 16.88 mmol) was added, and the mixture was refluxed for 18 hours. The product was partitioned between ethyl acetate and water, the organic layer washed with brine, dried over sodium sulfate, and solvent removed under reduced pressure. The residue was chromatographed on silica gel, eluting with ethyl acetate/hexane 1:1, to provide ethyl 4-methyl-2-[(methylamino)carbonylamino]-thiophene-3-carboxylate as pink crystals.

後処理

  1. temperaturewas refluxed for 1 hour
  2. temperaturethe mixture was refluxed for 18 hours
  3. customThe product was partitioned between ethyl acetate and water
  4. washthe organic layer washed with brine
  5. dry with materialdried over sodium sulfate, and solvent
  6. customremoved under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. washeluting with ethyl acetate/hexane 1:1

出典と根拠

ORDレコード
ord-d342891077d542e0be0f599352023051
出典データセット
uspto-grants-2010_08
特許番号
US07776868B2

関連ノート

読み込み中…