2-Chlorobenzoyl isocyanate → HCID 21873097, compound

HRID 1702999Notes

Reaction equation

HRID 1702999 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[C:13]1([CH:19]([O:21][C:22]2[CH:28]=[CH:27][C:25]([NH2:26])=[CH:24][CH:23]=2)[CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([NH:6][C:7]([NH:26][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH3:20])=[CH:28][CH:27]=1)=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 99423112-Chlorobenzoyl isocyanateHCID 2052442557181-91-6

Product 1

HCID 21873097HCID 21873097, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

18.7 g of 2-chlorobenzoylisocyanate were added to 150 ml of a solution of 23.4 g of 4-(1-phenylethoxy)aniline in dry acetonitrile. After stirring at room temperature for a few hours, the crystalline precipitate was sucked off, washed with successively acetonitrile, ethanol and petroleum ether and dried in air. The desired product was obtained in a yield of 32.8 g; melting point 166°-167° C. The starting aniline was obtained from the corresponding nitro compound by hydrogenation with hydrogen under the influence of Raney nickel as a catalyst in alcohol as a solvent. α-Methylbenzyl-4-nitrophenyl ether was prepared from a reaction of 1-bromo-1-phenyl-ethane and 4-nitrophenol under the influence of anhydrous potassium carbonate in acetone as a solvent.

Workup

  1. washwashed with successively acetonitrile, ethanol and petroleum ether
  2. customdried in air

Sources & evidence

ORD record
ord-5a09830974094ef0a1d79d95ba5f0315
Source dataset
uspto-grants-1982_09
Patent number
US04350706

Reaction notes

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