Hydrazine → HCID 24861016, compound

HRID 1990978Notes

Reaction equation

HRID 1990978 reaction equation
[CH3:1][N:2]([CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])C(=O)OC.NN.[OH-].[K+]>C(O)CO.O>[CH3:1][NH:2][CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:19])=[O:20]

Participants

6

Reactant 3

HCID 9321HydrazineHCID 14797Potassium HydroxideHCID 58955126HCID 58955126, compound

Product 1

HCID 24861016HCID 24861016, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of methyl methyl{2-[3-(phenylsulfonyl)-1H-indol-5-yl]ethyl}carbamate (171 mg, 0.46 mmol) in ethylene glycol (5 ml) was added H2NNH2 (147 mg, 4.6 mmol), KOH (1.9 g 13.8 mmol), and heated to 110° C. for 12 hours. The mixture was cooled to room temperature, diluted with water (5 mL) and extracted with EtOAc. The combined organic layers were washed with water (7 mL), brine (10 mL), dried (MgSO4), filtered and concentrated under reduced pressure to a residue which is triturated with CH2Cl2 to afford an off white solid, (131 mg, 93%). Mp: 151-154° C., MS (ES−) 313 (M−H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water (7 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue which
  7. customis triturated with CH2Cl2
  8. customto afford an off white solid, (131 mg, 93%)

Sources & evidence

ORD record
ord-3cb4c6e1d4ba4381a0cb107c7963eb65
Source dataset
uspto-grants-2010_01
Patent number
US07645752B2

Reaction notes

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