1,4-Dichlorobenzene → HCID 20465756, compound

HRID 2290953Notes

Reaction equation

HRID 2290953 reaction equation
C1(=O)O[CH:4]([CH3:5])[CH2:3]O1.C1C(Cl)=CC=C(Cl)C=1.[CH3:16][C:17]1[C:26]2[C:21](=CC=C[CH:25]=2)C=[CH:19][CH:18]=1.[NH:27]=[C:28]=[O:29]>C(S(O)(=O)=O)(F)(F)F.ClC1C=CC=CC=1.C1C=CC=CC=1.C1(C)C=CC=CC=1.C1(C)C(C)=CC=CC=1>[N-:27]=[C:28]=[O:29].[N-:27]=[C:28]=[O:29].[CH:4]1([CH3:5])[CH2:19][CH2:18][CH:17]([CH:26]([CH3:21])[CH3:25])[CH2:16][CH2:3]1

Participants

10

Reactant 4

HCID 46851,4-DichlorobenzeneHCID 6347Isocyanic acid2×HCID 70021-MethylnaphthaleneHCID 7924Propylene Carbonate

Product 1

HCID 20465756HCID 20465756, compoundYield 16%

Reagents, catalysts & solvents 5

HCID 62406Trifluoromethanesulfonic acidCatalystHCID 241BenzeneSolventHCID 1140TolueneSolvent2×HCID 7237O-XyleneSolventHCID 7964ChlorobenzeneSolvent

Procedure

Some mixed solvents such as mixtures of propylene carbonate and toluene and mixtures of one or more organic carbonates with solvents such as xylene, toluene, benzene, chlorobenzene, dichlorobenzene, methylnaphthalene, and nitro hydrocarbons can be used effectively as solvents in the process of this invention. The process of this invention can be run at temperatures below 0 degrees C. using excess liquid HNCO as solvent. For instance, the reaction of alpha-terpinyl isocyanate with an excess of HNCO using CF3SO3H as catalyst at -20 degrees C. for 2 hours gave a 16% yield of menthane diisocyanate with a selectivity of 80%.

Workup

  1. customcan be run at temperatures below 0 degrees C
  2. customat -20 degrees C

Sources & evidence

ORD record
ord-4f5ebb6e8aa7498fa1ff27408707adae
Source dataset
uspto-grants-1986_10
Patent number
US04618707

Reaction notes

Loading…