Acetic Acid → HCID 86762102, compound

HRID 1045095Notes

Reaction equation

HRID 1045095 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:5]=[C:6]([NH2:19])[C:7]([NH2:18])=[CH:8][C:9]=1[C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:20](=S)=[S:21].CC(O)=O>CCO.O>[Cl:3][C:4]1[C:9]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][C:7]2[NH:18][C:20](=[S:21])[NH:19][C:6]=2[CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6348Carbon DisulfideHCID 14797Potassium Hydroxide2×HCID 58387126HCID 58387126, compound

Product 1

HCID 86762102HCID 86762102, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

A 2 mL Biotage™ microwave vial was charged with solid KOH (19.4 mg, 0.345 mmol), water (0.2 mL), a solution of compound 1-2 (55.8 mg, 0.230 mmol) in EtOH (1.2 mL) and carbon disulfide (69 uL, 1.2 mmol). The vial was capped and stirred at rt until KOH dissolved, and then heated in a microwave synthesizer (Biotage Initiator™) at 110° C. for 10 min. Contents of the vial were transferred to a 20 mL scintillation vial, diluted with water (8 mL) and acidified by the dropwise addition of 10% aqueous AcOH. The resulting suspension was centrifuged, the supernatant was decanted and the resulting brownish precipitate was washed with 10% aqueous AcOH (3 mL) and water (three times 3 mL). The precipitate was dissolved in EtOAc and passed through a short plug of neutral alumina. The EtOAc solution was evaporated to dryness in vacuo to give the crude product as brownish solid. LR-MS (API-ES): calculated for C15H9ClN2S 284.0, observed m/e 285.0 (M+H)+. (Rt 2.94 min). The crude product was used in the next step without further purification.

Workup

  1. customThe vial was capped
  2. dissolutiondissolved
  3. customthe supernatant was decanted
  4. washthe resulting brownish precipitate was washed with 10% aqueous AcOH (3 mL) and water (three times 3 mL)
  5. dissolutionThe precipitate was dissolved in EtOAc
  6. customThe EtOAc solution was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-845a23a921b449deb525d27014531363
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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