Methylhydrazine → HCID 22419542, compound

HRID 1197398Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:12](O)=[O:13])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.CS(Cl)(=O)=O.[CH3:44][NH:45][NH2:46]>ClCCl>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[CH:10]=[C:11]([CH:15]=[CH:16][C:17]=2[O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:12]([N:45]([CH3:44])[NH2:46])=[O:13])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -40 °C

Procedure

3,4-bis-(4-Methoxybenzyloxy)benzoic acid (0.792 g, 2.0 mmol) was dissolved in dichloromethane (20 ml) and treated with N,N-diisopropylethylamine (0.35 ml, 2.0 mmol). The solution was cooled to -40° C. and treated with methanesulphonyl chloride (0.15 ml, 2.0 mmol). The mixture was allowed to warm to room temperature for 10 minutes and then re-cooled to -40° C. and added to a solution of methylhydrazine (0.215 ml, 4 mmol) in dichloromethane (10 ml) at -40° C. The mixture was allowed to warm to room temperature for 1.5 h and then evaporated to dryness under reduced pressure. The residue was dissolved in ethyl acetate which was washed with water and brine. Evaporation of the solvent gave the title compound (0.823 g, 94%); δH (CDCl3) 3.08 (3H, s), 3.74 (6H, s), 4.25 (2H, brs), 5.03 (4H, s), and 6.70- 7.40 (11H, m).

Workup

temperatureto warm to room temperature for 10 minutes
temperaturere-cooled to -40° C.
temperatureto warm to room temperature for 1.5 h
customevaporated to dryness under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate which
washwas washed with water and brine
customEvaporation of the solvent

Sources & evidence

ORD record: ord-f267707265924546bdb3275f3cd29697
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05275816

Reaction notes

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