Phenylacetic Acid → Methyl 2-(N-tert-butylsulfamoyl)-4-(2-phenylacetylhydrazino)benzoate

HRID 1457521Notes

Reaction equation

C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([NH:20][S:21]([C:24]1[CH:33]=[C:32]([NH:34][NH2:35])[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27])(=[O:23])=[O:22])([CH3:19])([CH3:18])[CH3:17].[C:36]1([CH2:42][C:43](O)=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:16]([NH:20][S:21]([C:24]1[CH:33]=[C:32]([NH:34][NH:35][C:43](=[O:44])[CH2:42][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27])(=[O:23])=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

Conditions

Temperature: 25 °C

Procedure

1.5 g (7.3 mmol) of dicyclohexylcarbodiimide (DCC) are added to a solution of 2.0 g (6.6 mmol) of methyl 2-(N-tert-butylsulfamoyl)-4-hydrazinobenzoate, 0.9 g (6.6 mmol) of phenylacetic acid and 0.03 g of 4-dimethylaminopyridine (DMAP) in 20 ml of CH2Cl2 at 0° C. The mixture is stirred at 25° C. for 15 hours, the solid is filtered off with suction and the organic phase is washed successively with water, 1N HCl and NaHCO3 solution, dried and evaporated. This gives 1.6 g (58% of theory) of methyl 2-(N-tert-butylsulfamoyl)-4-(2-phenylacetyl-hydrazino)benzoate with the following nuclear magnetic resonance data:

Workup

filtrationthe solid is filtered off with suction
washthe organic phase is washed successively with water, 1N HCl and NaHCO3 solution
customdried
customevaporated

Sources & evidence

ORD record: ord-9a03cf7953de43f692f15e8c305b3e35
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849666

Reaction notes

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