Hydrazine → 3-iodo-1-tosyl-1H-indole-5-carbohydrazide

HRID 634193Notes

Reaction equation

HRID 634193 reaction equation
O.[N:2]1(O)C2C=CC=CC=2N=[N:3]1.Cl.C(N=C=NCCCN(C)C)C.[I:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:34](O)=[O:35])[CH:32]=2)[N:27]([S:37]([C:40]2[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=2)(=[O:39])=[O:38])[CH:26]=1.NN>CN(C=O)C>[I:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:34]([NH:2][NH2:3])=[O:35])[CH:32]=2)[N:27]([S:37]([C:40]2[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=2)(=[O:39])=[O:38])[CH:26]=1

Participants

6

Reactant 4

HCID 9321HydrazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 683285993-iodo-1-tosyl-1H-indole-5-carboxylic acid

Product 1

HCID 683285283-iodo-1-tosyl-1H-indole-5-carbohydrazideYield 68.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1H-benzo[d][1,2,3]triazol-1-ol hydrate (0.471 g, 3.07 mmol) (Aldrich), N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.589 g, 3.07 mmol) (Sigma-Aldrich), and 3-iodo-1-tosyl-1H-indole-5-carboxylic acid (1.13 g, 2.56 mmol) were weighed into a 100 mL round bottomed flask and dissolved in DMF (12 mL). The solution was stirred at RT for 30 min. Hydrazine (1.4 mL, 44.6 mmol) (Aldrich) was added, and the reaction was stirred at RT for 1.5 h. The solution was partially concentrated. The concentrate was diluted with H2O and a precipitate formed. The solid was collected by filtration, washed with H2O, and dried to give 3-iodo-1-tosyl-1H-indole-5-carbohydrazide (0.802 g, 1.762 mmol, 68.8%) as a beige solid. MS (ESI, pos. ion) m/z: 455.9 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.91 (s, 1H), 8.15 (s, 1H), 7.97-8.02 (m, 1H), 7.95 (d, J=8.4 Hz, 2H), 7.82-7.92 (m, 2H), 7.41 (d, J=8.2 Hz, 2H), 4.52 (br. s., 1H), 2.33 (s, 3H).

Workup

  1. stirringthe reaction was stirred at RT for 1.5 h
  2. concentrationThe solution was partially concentrated
  3. additionThe concentrate was diluted with H2O
  4. customa precipitate formed
  5. filtrationThe solid was collected by filtration
  6. washwashed with H2O
  7. customdried

Sources & evidence

ORD record
ord-2671a0d5a6c049f291e9d786ace1a7b9
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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