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

HRID 275096Notes

Reaction equation

HRID 275096 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].[CH3:34]C(C)=O>>[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 180Acetone2×HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 15766649Bis(2-chloro-4-fluoro-5-aminophenyl)carbonate

Product 1

HCID 15766844Bis(2-chloro-4-fluoro-5-methoxycarbonylaminophenyl)carbonateYield 88.2%

Conditions

Temperature
60 °C

Procedure

Dry acetone (1500 ml) was added to a mixture comprising bis(2-chloro-4-fluoro-5-aminophenyl)carbonate (233 g, 0.68 mol) and potassium carbonate (188 g, 1.36 mol), and methyl chloroformate (126 g, 1.33 mol) was dropwise added to the resulting solution, and the mixture was heated at 60° C. for 4 hours with stirring. After reaction, acetone was removed by distillation under reduced pressure, acetic acid was added so that the reaction mixture was made acidic, and thereafter the acidic mixture was poured into ice-water. The solid as precipitated out was taken out by filtration, washed with water and fully dried to obtain a white solid of bis(2-chloro-4-fluoro-5-methoxycarbonylaminophenyl)carbonate (279 g, 0.60 mol). Yield: 88.2%. Spectral data and other data of the product are those as shown in Example 11.

Workup

  1. additionwas dropwise added to the resulting solution
  2. customwas removed by distillation under reduced pressure, acetic acid
  3. additionwas added so that the reaction mixture
  4. additionthe acidic mixture was poured into ice-water
  5. customThe solid as precipitated
  6. filtrationout was taken out by filtration
  7. washwashed with water
  8. customfully dried

Sources & evidence

ORD record
ord-949c16b1211b4dc5a2bb256a389f2770
Source dataset
uspto-grants-1995_02
Patent number
US05391807

Reaction notes

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