3,4-Dichlorophenyl isocyanate → HCID 21414095, compound

HRID 442293Notes

Reaction equation

HRID 442293 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:12][NH:13][S:14]([CH2:17][Cl:18])(=[O:16])=[O:15].C(N(CC)CC)C>C(OCC)C>[CH3:12][N:13]([S:14]([CH2:17][Cl:18])(=[O:16])=[O:15])[C:10]([NH:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1)=[O:11]

Participants

5

Reactant 3

HCID 76073,4-Dichlorophenyl isocyanateHCID 8471TriethylamineHCID 1795321-Chloro-N-methylmethanesulfonamide

Product 1

HCID 21414095HCID 21414095, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of 19 g of 3,4-dichlorophenyl isocyanate in 150 ml of ethyl ether was added to a solution of 14.4 g of N-methyl-N-chloromethylsulfonyl-amine in 150 ml of ethyl ether and after the addition of 0.1 ml of triethylamine, the mixture was stirred for a hour at 20° C. The crystals formed were recovered by vacuum filtration, were washed, dried and dissolved in chloroform. The insolubles were removed by filtration and the filtrate was concentrated to dryness. The product was crystallized from methyl ethyl ketone to obtain 21.3 g of N-methyl-N-chloromethylsulfonyl-N'-(3,4-dichlorophenyl)-urea melting at 119° C.

Workup

  1. customThe crystals formed
  2. filtrationwere recovered by vacuum filtration
  3. washwere washed
  4. customdried
  5. dissolutiondissolved in chloroform
  6. customThe insolubles were removed by filtration
  7. concentrationthe filtrate was concentrated to dryness
  8. customThe product was crystallized from methyl ethyl ketone

Sources & evidence

ORD record
ord-40768e7fe4a749beb6df42580dc6c1e7
Source dataset
uspto-grants-1977_08
Patent number
US04045209

Reaction notes

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