Dichloromethane → HCID 13852481, compound

HRID 330445Notes

Reaction equation

HRID 330445 reaction equation
[NH2:1][S:2]([C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[C:7]([O:9][CH2:10][CH2:11][OH:12])=[O:8])(=[O:4])=[O:3].C(Cl)Cl.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22]>C(N(CC)CC)C>[NH2:1][S:2]([C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[C:7]([O:9][CH2:10][CH2:11][O:12][Si:21]([CH3:23])([CH3:22])[CH3:20])=[O:8])(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6397ChlorotrimethylsilaneHCID 138524802-Hydroxyethyl 2-sulfamoylbenzoate

Product 1

HCID 13852481HCID 13852481, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a slurry of 12.25 g of 2-aminosulfonylbenzoic acid, 2-hydroxyethyl ester, 125 ml of dry methylene chloride, and 7.7 ml of triethylamine was added dropwise over 10 minutes 6.3 ml of trimethylsilyl chloride (exotherm to 36° C.). The resulting solution was allowed to stand at ambient temperature for 18 hours and then washed with saturated sodium chloride solution, dried (MgSO4), and the solvent removed under reduced pressure to give an oil which was chromatographed on silica gel eluting with 25% EtOAc:hexane to give a colorless oil which slowly crystallized. Trituration with hexane gave 8.0 g of white crystals, m.p. 72°-76° C.

Workup

  1. washwashed with saturated sodium chloride solution
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customto give an oil which
  5. customwas chromatographed on silica gel eluting with 25% EtOAc
  6. customhexane to give a colorless oil which
  7. customslowly crystallized

Sources & evidence

ORD record
ord-167755113bc64f619c8545a859e05349
Source dataset
uspto-grants-1990_01
Patent number
US04897108

Reaction notes

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