Ethanol → HCID 20159085, compound

HRID 986036Notes

Reaction equation

HRID 986036 reaction equation
C(O)C.[N+:4]([C:7]1[CH:12]=[CH:11][C:10]([N:13]=[C:14]=[O:15])=[CH:9][CH:8]=1)([O-:6])=[O:5].[CH2:16]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[CH2:17][CH3:18]>C(#N)C>[N+:4]([C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14]([N:19]([C:20]2[CH:21]=[CH:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[CH2:16][CH2:17][CH3:18])=[O:15])=[CH:11][CH:12]=1)([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 66012Benzene, 1-isocyanato-4-nitro-HCID 1251290973938-86-0

Product 1

HCID 20159085HCID 20159085, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.09 g of 2-chlorobenzoylisocyanate was added to a solution of 2.00 g of N-(4-aminophenyl)-N'-(4-chlorophenyl)-N'-propylurea in 50 ml of acetonitrile while stirring at room temperature. After stirring for 1.5 hours at room temperature the formed precipate was sucked off, washed with diethyl ether, and dried. According to PMR the product had the desired structure; the product melted at 170° C. The starting aniline was obtained from the corresponding nitro compound by reduction with hydrogen under the influence of Raney nickel as a catalyst; in this reaction ethanol was used as a solvent. N-(4-nitrophenyl)-N'-(4-chlorophenyl)-N'-propylurea was prepared by a coupling of p-nitrophenylisocyanate with N-propyl-4-chloroaniline in acetonitrile as a solvent. In a corresponding manner, in which, if desired, instead of acetonitrile diethyl ether was used as a solvent for the first-mentioned reaction, the following compounds were prepared; the compound numbers corresponding again with the numbers given before in the specification:

Workup

  1. customwas used as a solvent for the first-mentioned reaction
  2. customthe following compounds were prepared

Sources & evidence

ORD record
ord-2bb50bb5571e468c873da0ae409f58e1
Source dataset
uspto-grants-1987_12
Patent number
US04710516

Reaction notes

Loading…