Acetic Acid → 2-[3-(4-Phenoxy-phenyl)-ureido]-thiophene-3-carboxylic acid tert-butyl ester

HRID 2217158

Reaktionsgleichung

Reaktionsgleichung von HRID 2217158
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].[O:14]([C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O.C(O)(=O)C>N1C=CC=CC=1>[C:10]([O:9][C:7]([C:6]1[CH:5]=[CH:4][S:3][C:2]=1[NH:1][C:28]([NH:27][C:24]1[CH:25]=[CH:26][C:21]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:22][CH:23]=1)=[O:29])=[O:8])([CH3:13])([CH3:12])[CH3:11]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 962WaterHCID 27348964-Phenoxyphenyl isocyanateHCID 10845692Tert-butyl 2-aminothiophene-3-carboxylate

Produkt 1

HCID 866265972-[3-(4-Phenoxy-phenyl)-ureido]-thiophene-3-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of t-butyl 2-amino-thiophene-3-carboxylate (0.6 g) in dry pyridine (20 ml) was added 4-phenoxyphenylisocyanate (0.84 g). The mixture was stirred for 48 h, then the dark coloured solution was poured into water (200 ml). The stirred mixture was acidified with acetic acid and a precipitate slowly solidified to give a brown solid. After about 1 hr, the solid was filtered off, dried in vacuo and recrystallised from acetonitrile, giving an off-white solid. MP=203-205° C. Yield=0.6 g (48.8%).

Aufarbeitung

  1. customto give a brown solid
  2. waitAfter about 1 hr
  3. filtrationthe solid was filtered off
  4. customdried in vacuo
  5. customrecrystallised from acetonitrile
  6. customgiving an off-white solid

Quellen und Nachweise

ORD-Eintrag
ord-6ad5334a3b634aec83faf421a488e937
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407954B2

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