Methanol → HCID 17755357, compound

HRID 1667050Notes

Reaction equation

HRID 1667050 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]2[CH:18]=1)([O-])=O.S.[Na].CO.O>C(Cl)Cl>[N:11]1[C:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH2:1])=[CH:18][N:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=12

Participants

6

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 596799982-(2-Nitrophenyl)imidazo[1,2-a]pyridineHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 17755357HCID 17755357, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Sulfide reduction. Into a round bottom flask was charged 2-(2-Nitro-phenyl)-imidazo[1,2-a]pyridine (250 mg, 1.04 mmol), Sodium hydrogensulfide (351 mg, 6.24 mmol), methanol (6 ml) and water (2 ml). The reaction mixture was refluxed overnight. TLC indicated that the reaction was complete (5% MeOH in CH2Cl2). The mixture was cooled to room temperature, concentrated to dryness and to the white/yellow salts was added water (1 mL), CH2Cl2 (10 mL) and MeOH (1 mL). The layers were separated and the aqueous layer was back extracted with CH2Cl2 (2×10 ml). The combined organic layers were dried over Na2SO4, and concentrated to dryness to obtain the product as a tan solid (MS, M++H=210.1).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated to dryness and to the white/yellow salts
  3. additionwas added water (1 mL), CH2Cl2 (10 mL) and MeOH (1 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was back extracted with CH2Cl2 (2×10 ml)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-84d64b59f56e42409e53304af679d8c4
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

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