Reaktion #2991

ord-b9a7eb44685f468d8f6ff10d7448f0ce

Reaktionsgleichung

[H][H]
hydrogen
C#Cc1cc(C)c(C(=O)N=C(N)N)cc1S(C)(=O)=O
N-diaminomethylene-2-methyl-4-ethynyl-5-methylsulfonylbenzamide
COC(=O)c1cc(S(C)(=O)=O)c(Br)cc1C
methyl 2-methyl-4-bromo-5-methylsulfonyl-benzoate
C#Cc1cc(C)c(C(=O)OC)cc1S(C)(=O)=O
methyl 2-methyl-4-ethynyl-5-methylsulfonyl-benzoate
N=C(N)N
guanidine
→
C=Cc1cc(C)c(C(=O)N=C(N)N)cc1S(C)(=O)=O
N-diaminomethylene-2-methyl-4-ethenyl-5-methylsulfonyl-benzamide

Edukte

[H][H]
hydrogen
—
Li acetylide
C#Cc1cc(C)c(C(=O)N=C(N)N)cc1S(C)(=O)=O
N-diaminomethylene-2-methyl-4-ethynyl-5-methylsulfonylbenzamide
COC(=O)c1cc(S(C)(=O)=O)c(Br)cc1C
methyl 2-methyl-4-bromo-5-methylsulfonyl-benzoate
C#Cc1cc(C)c(C(=O)OC)cc1S(C)(=O)=O
methyl 2-methyl-4-ethynyl-5-methylsulfonyl-benzoate
N=C(N)N
guanidine

Reagenzien

O=C([O-])[O-].[Ca+2].[Pd]
Pd CaCO3

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

6.0 g of N-diaminomethylene-2-methyl-4-ethynyl-5-methylsulfonylbenzamide, m.p. 223°-226° [obtainable by reaction of methyl 2-methyl-4-bromo-5-methylsulfonyl-benzoate with Li acetylide to give methyl 2-methyl-4-ethynyl-5-methylsulfonyl-benzoate and subsequent reaction with guanidine] are dissolved in 300 ml of DMF and hydrogenated in the presence of 450 mg of Pd-CaCO3 (Lindlar catalyst) for 15 minutes in a stream of hydrogen (p=1 bar). Customary working up gives N-diaminomethylene-2-methyl-4-ethenyl-5-methylsulfonyl-benzamide).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731351uspto-grants-1998_03