Acetic Acid → HCID 86762103, compound

HRID 1045098Notes

Reaction equation

HRID 1045098 reaction equation
[OH-].[K+].[Cl:3][C:4]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:12][CH:11]=2)=[CH:8][C:7]([NH2:22])=[C:6]([NH2:23])[CH:5]=1.[C:24](=S)=[S:25].CC(O)=O>CCO.O>[C:13]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]([C:9]2[C:4]([Cl:3])=[CH:5][C:6]3[NH:23][C:24](=[S:25])[NH:22][C:7]=3[CH:8]=2)=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6348Carbon DisulfideHCID 14797Potassium Hydroxide2×HCID 58387188HCID 58387188, compound

Product 1

HCID 86762103HCID 86762103, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

A 2 mL Biotage™ microwave was charged with solid KOH (18.0 mg, 0.326 mmol), water (0.2 mL), a solution of compound 2-2 (64.0 mg, 0.217 mmol) in EtOH (1.2 mL) and carbon disulfide (65 uL, 1.1 mmol). The vial was capped and stirred at rt until KOH dissolved 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 (6 mL) and acidified by a 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 then 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 yellow solid. LR-MS (API-ES): calculated for C19H13ClN2S 336.1, observed m/e 337.0 (M+H)+ (Rt 3.12 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 then dissolved in EtOAc
  6. customThe EtOAc solution was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-ec59715345684586a33a52e592db6dc2
Source dataset
uspto-grants-2013_10
Patent number
US08563746B2

Reaction notes

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