Toluene → Bis(2-chloro-4-fluoro-5-methoxycarbonylaminophenyl)carbonate

HRID 742430Notes

Reaction equation

HRID 742430 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH2:9])=[CH:4][C:3]=1[O:10][C:11](=[O:22])[O:12][C:13]1[CH:18]=[C:17]([NH2:19])[C:16]([F:20])=[CH:15][C:14]=1[Cl:21].[C:23](=[O:26])([O-:25])[O-].[K+].[K+].Cl[C:30]([O:32][CH3:33])=[O:31].[C:34]1(C)C=CC=CC=1>>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([NH:9][C:23]([O:25][CH3:34])=[O:26])=[CH:4][C:3]=1[O:10][C:11](=[O:22])[O:12][C:13]1[CH:18]=[C:17]([NH:19][C:30]([O:32][CH3:33])=[O:31])[C:16]([F:20])=[CH:15][C:14]=1[Cl:21]

Participants

5

Reactant 4

HCID 1140TolueneHCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 15766649Bis(2-chloro-4-fluoro-5-aminophenyl)carbonate

Product 1

HCID 15766844Bis(2-chloro-4-fluoro-5-methoxycarbonylaminophenyl)carbonateYield 90.2%

Procedure

Bis(2-chloro-4-fluoro-5-aminophenyl)carbonate (1.75 Kg, 5.0 mol), potassium carbonate (1.04 Kg, 7.5 mol) and toluene (6 liters) as a solvent were placed in a 10L three-necked flask equipped with a stirrer and a dropping funnel. To the resulting solution was added dropwise methyl chloroformate (770 ml, 9.9 mol), and the mixture was stirred at 60°-70° C. (a bath temperature) for 5 hours. After completion of the reaction, the reaction mixture was filtered, washed with toluene, 1N hydrochloric acid and water, and thoroughly dried to obtain bis(2-chloro-4-fluoro-5-methoxycarbonylaminophenyl)carbonate as a white solid (2.10 Kg, 4.51 mol, 90.2% yield).

Workup

  1. customequipped with a stirrer and a dropping funnel
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered
  4. washwashed with toluene, 1N hydrochloric acid and water
  5. customthoroughly dried

Sources & evidence

ORD record
ord-6882a62c344048baa8492a3ad2ae0186
Source dataset
uspto-grants-1996_09
Patent number
US05554581

Reaction notes

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