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

HRID 2401143Notes

Reaction equation

HRID 2401143 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 C6H3ClIN3S 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-07e88a516c354abca3ac80d32e2492ed
Source dataset
uspto-grants-2014_08
Patent number
US08796258B2

Reaction notes

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