Methyl chloroformate → HCID 178502262, compound

HRID 1047104Notes

Reaction equation

HRID 1047104 reaction equation
[C:1]1(N)[C:6](F)=[C:5](F)[C:4](F)=[C:3]([NH2:10])[C:2]=1F.[ClH:13].[ClH:14].[CH2:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH3:16].Cl[C:23]([O:25][CH3:26])=[O:24]>ClCCl>[CH3:26][O:25][C:23](=[O:24])[NH:10][C@H:3]1[CH2:4][CH2:5][C@H:6]([CH2:16][CH2:15][N:17]2[CH2:20][CH2:21][N:10]([C:3]3[CH:4]=[CH:5][CH:6]=[C:1]([Cl:13])[C:2]=3[Cl:14])[CH2:19][CH2:18]2)[CH2:1][CH2:2]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochloride

Product 1

HCID 178502262HCID 178502262, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
22.5 °C

Procedure

6.45 g (0.015 mol) of dihydrochloride of compound of formula (III) was added to a mixture of 125 ml dichloromethane and 12.25 ml triethylamine and the thick suspension obtained was stirred at a temperature between 20-25° C. for one hour. The so obtained suspension was added to a solution of 2.3 ml (0.03 mol) methyl chloroformate in 25 ml of dichloromethane at a temperature between 5-10° C. The reaction mixture obtained was stirred at a temperature between 20-25° C. for 3 hours then extracted with 3×150 ml (150 g) of distilled water. The organic phase was evaporated in vacuum and the residue was recrystallized from methanol. In this manner 4.5 g of the title product was obtained.

Workup

  1. customthe thick suspension obtained
  2. customThe so obtained suspension
  3. customThe reaction mixture obtained
  4. stirringwas stirred at a temperature between 20-25° C. for 3 hours
  5. extractionthen extracted with 3×150 ml (150 g) of distilled water
  6. customThe organic phase was evaporated in vacuum
  7. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-945f56454cf74442b0f9d83dc8c14624
Source dataset
uspto-grants-2013_10
Patent number
US08569498B2

Reaction notes

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