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Thiophosgene → 6-Chloro-5-iodo-1H-imidazo[4,5-b]pyridine-2(3H)-thione

HRID 929171
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 929171
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[N:6][C:7]=1[I:8].[C:11](Cl)(Cl)=[S:12]>CN(C1C=CN=CC=1)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:10][C:11](=[S:12])[NH:9][C:5]2=[N:6][C:7]=1[I:8]
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Komponenten

5

Edukt 2

HCID 10040ThiophosgeneHCID 772305535-Chloro-6-iodopyridine-2,3-diamine

Produkt 1

HCID 866847396-Chloro-5-iodo-1H-imidazo[4,5-b]pyridine-2(3H)-thione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

DMAP (15.4 g, 126 mmol) was added to a THF (200 mL) solution of 5-chloro-6-iodopyridine-2,3-diamine (17 g, 63.1 mmol). Thiophosgene (4.9 mL, 63.1 mmol) was then added drop-wise via addition funnel under nitrogen and allowed to stir at rt for 1 h. The mixture was then partitioned between ethyl acetate (500 mL) and 2N HCl (100 mL). The ethyl acetate layer was washed with brine, dried over magnesium sulfate and concentrated to give the desired product as a white powder, which was used in the next step without further purification. LC-MS: calculated for C6H3ClIN3S 311.5, observed m/e: 311.91 (M+H)+ (Rt 1.69/5 min)

Aufarbeitung

  1. additionvia addition funnel under nitrogen
  2. customThe mixture was then partitioned between ethyl acetate (500 mL) and 2N HCl (100 mL)
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-5823cfbb91f34b3486b28dcebd4ed834
Quelldatensatz
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09290517B2

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