Hydrochloric Acid → 2-[N-(2,4,6-trifluorophenyl)sulfamoyl]-acetic acid methyl ester

HRID 654006Notes

Reaction equation

HRID 654006 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].N1C=CC=CC=1.[CH3:17][O:18][C:19](=[O:25])[CH2:20][S:21](Cl)(=[O:23])=[O:22].Cl>ClC(Cl)C>[CH3:17][O:18][C:19](=[O:25])[CH2:20][S:21](=[O:23])(=[O:22])[NH:4][C:3]1[C:2]([F:1])=[CH:8][C:7]([F:9])=[CH:6][C:5]=1[F:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 677652,4,6-TrifluoroanilineHCID 11435213Methyl (chlorosulfonyl)acetate

Product 1

HCID 150576002-[N-(2,4,6-trifluorophenyl)sulfamoyl]-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.76 g (5 mmol) of 2,4,6-trifluoroaniline is dissolved in 40 ml of dichloroethane with exclusion of moisture, 0.4 ml (5 mmol) of pyridine is added, 0.86 g (5 mmol) of chlorosulfonyl acetic acid methyl ester, dissolved in 10 ml of dichloroethane, is instilled at 0° C. and then it is stirred for 1 hour at 0° C. and 12 hours at room temperature. The reaction solution is then shaken out twice with 10 ml of 2N hydrochloric acid each, the phases are separated, the organic phase is dried on magnesium sulfate, filtered and evaporated to dryness. The residue is crystallized from diethyl ether/pentane 1:1. 790 mg (2.79 mmol)=55.79% of the theoretical yield is obtained as a crystallizate. Melting point 99-100° C.

Workup

  1. additionis added
  2. customis instilled at 0° C.
  3. customare separated
  4. customthe organic phase is dried on magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue is crystallized from diethyl ether/pentane 1:1
  8. custom790 mg (2.79 mmol)=55.79% of the theoretical yield
  9. customis obtained as a crystallizate

Sources & evidence

ORD record
ord-87ef31eb74b042b9b9e337b1bd335be7
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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