Methanesulfonic Acid → HCID 86628489, compound

HRID 968848Notes

Reaction equation

HRID 968848 reaction equation
[CH2:1]([NH:4][C:5]([N:7]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[NH:8]C(OC(C)(C)C)=O)=[O:6])[CH2:2][CH3:3].[CH3:23][S:24]([OH:27])(=[O:26])=[O:25]>ClCCl>[CH3:23][S:24]([OH:27])(=[O:26])=[O:25].[CH2:1]([NH:4][C:5]([N:7]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[NH2:8])=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 59015843HCID 59015843, compound

Product 1

HCID 86628489HCID 86628489, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Propylaminocarbonyl)-2-(phenylmethyl)hydrazine carboxylic acid, 1,1-dimethylethyl ester (2.33 g, 7.58 mmol) was dissolved in dichloromethane (25 mL). Methanesulfonic acid (615 μL, 9.48 mmol) was added in one portion and the solution was allowed to stir at rt overnight. The solution was heated to reflux for 8 h, then concentrated to afford the title compound as a crude white solid (2.47 g, 107%): mp 78.1-82.9° C.; 1H NMR (DMSO-d6) δ 9.7 (br s, 3H), 7.61 (br s, 1H), 7.38 (t, 1H, J=8 Hz), 7.32 (m, 4H), 4.74 (s, 2H), 3.07 (t, 2H, J=8 Hz), 2.38 (s, 3H), 1.43, (quint, 2H, J=8 Hz), 0.81 (t, 3H, J=8 Hz); 13C NMR (DMSO-d6) δ 157.5, 135.6, 129.3, 128.7, 128.6, 52.8, 42.7, 40.3, 23.3, 11.9; IR (CHCl3) 3009, 1691, 1543, 1196 cm−1; Exact Mass Calcd. For C11H17N3O: 208.1450. Found: 208.1462.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 8 h
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-10c770c9f97b4e62af17df96ec246996
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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