1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-(1,2,4-Triazol-1-ylmethylcarbonylamino)dibenzothiophene

HRID 1063999

Reaktionsgleichung

Reaktionsgleichung von HRID 1063999
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[N:15]1([CH2:20][C:21](O)=[O:22])[CH:19]=[N:18][CH:17]=[N:16]1.O.ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C>O.CN(C=O)C>[N:15]1([CH2:20][C:21]([NH:1][C:2]2[CH:14]=[CH:13][C:5]3[S:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[C:4]=3[CH:3]=2)=[O:22])[CH:19]=[N:18][CH:17]=[N:16]1

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2984422-DibenzothiophenamineHCID 18101801,2,4-Triazole-1-acetic acidHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 222777952-(1,2,4-Triazol-1-ylmethylcarbonylamino)dibenzothiopheneAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Aminodibenzthiophene (Bull. Soc. Chim. Fr. (1 996), 133 (6), 597-610; 500 mg, 2.5 mmol) was dissolved DMF (10 ml) and 2-(1,2,4-triazol-1-yl)acetic acid (318 mg, 2.5 mmol) was added in one portion followed by 1-hydroxybenztriazole hydrate (383 mg, 5.0 mmol) and EDAC (960 mg, 5.0 mmol). The resultant mixture was stirred for 16 hours at ambient temperature then poured on to water (100 ml). A fine white solid was collected which was washed extensively with water, methanol (25 ml) and ether (25 ml) to leave a colourless solid (650 mg). NMR: 10.62 (brs, 1H), 8.18 (m, 2H), 8.16 (m, 3H), 7.99 (m,3H), 7.62 (dd, 1H), 7.50 (m, 2H), 5.20 (s, 2H); m/z 309.

Aufarbeitung

  1. additionwas added in one portion
  2. customA fine white solid was collected which
  3. washwas washed extensively with water, methanol (25 ml) and ether (25 ml)

Quellen und Nachweise

ORD-Eintrag
ord-a1c72c0c3a98429981c618db88f83ba0
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967216B2

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