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

HRID 1050255Notes

Reaction equation

HRID 1050255 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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 C6H3ClN3S 311.5, observed m/e: 311.91 (M+H)+ (Rt 1.69/5 min).

Workup

  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

Sources & evidence

ORD record
ord-7b62b5331cb64c65a920147df298e1f6
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

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