Methanesulfonic Acid → HCID 86628486, compound

HRID 968827Notes

Reaction equation

HRID 968827 reaction equation
[CH2:1]([NH:4][C:5]([N:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[NH:8]C(OC(C)(C)C)=O)=[O:6])[CH2:2][CH3:3].[CH3:24][S:25]([OH:28])(=[O:27])=[O:26]>ClCCl>[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].[CH2:1]([NH:4][C:5]([N:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1)[NH2:8])=[O:6])[CH2:2][CH3:3]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 59015853HCID 59015853, compound

Product 1

HCID 86628486HCID 86628486, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(propylaminocarbonyl)-2-(4-methylphenylmethyl)hydrazinecarboxylic acid, 1,1-dimethylethyl ester (3.0204 g, 9.397 mmol) in dichloromethane (25 mL) was added methanesulfonic acid (762 μL, 11.7 mmol) and the mixture stirred for 21 h. The mixture was then concentrated in vacuo to an oil and recrystallized (ethyl acetate) to afford the title compound as a white solid (2.0639 g, 6.502 mmol, 69%): mp 108.5-111.4° C.; 1H NMR (DMSO-d6) δ 7.56 (s, 1H), 7.18 (s, 4H), 4.67 (s, 2H), 3.06 (t, 2H, J=7.0 Hz), 2.35 (s, 3H), 2.81 (s, 3 H), 1.44 (m, 2H), 0.82 (t,. 3H, J=7.5 Hz); 13C NMR (DMSO-d6) δ 157.7, 138.0, 132.5, 129.9, 128.8, 52.7, 42.7, 40.6, 23.3, 21.4, 11.9; IR (CHCl3) 3416, 3009, 2967, 2936, 2877, 1691, 1543 cm−1. Anal. Calcd. for C12H19N3O.CH4O3S: C, 49.19; H, 7.30; N, 13.24. Found: C, 48.87; H, 7.32; N, 13.28.

Workup

  1. concentrationThe mixture was then concentrated in vacuo to an oil
  2. customrecrystallized (ethyl acetate)

Sources & evidence

ORD record
ord-4c6b8efe5d7a403aa14c76c74f1109bf
Source dataset
uspto-grants-2007_12
Patent number
US07304062B2

Reaction notes

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