Water → HCID 9813380, compound

HRID 327693Notes

Reaction equation

HRID 327693 reaction equation
Cl[S:2]([N:5]=C=O)(=[O:4])=[O:3].C1(C)C=CC=CC=1.[OH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1.O>O1CCCC1>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][C:16]([O:15][S:2]([NH2:5])(=[O:3])=[O:4])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 7456MethylparabenHCID 70918Chlorosulfonyl isocyanate

Product 1

HCID 9813380HCID 9813380, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Chlorosulfonylisocyanate (8.8 ml, 0.1 mole) was added to 200 ml toluene. Solid methyl 4-hydroxybenzoate (15.2 g, 0.1 mole) was added to the stirred solution. The mixture was heated at reflux for 1.5 hr then cooled and treated with about 8 ml water and some tetrahydrofuran. Solvents were then removed by evaporation. The residue was triturated with ethyl acetate-isopropyl ether. The insoluble solid was removed by filtration. The filtrate was concentrated and then triturated in isopropyl ether. The solid was collected and weighed 8.6 g. Recrystallization from acetone-isopropyl ether gave a white solid which was dried under vacuum overnight at room temperature to 3.9 g, mp 116°-118° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1.5 hr
  3. temperaturethen cooled
  4. customSolvents were then removed by evaporation
  5. customThe residue was triturated with ethyl acetate-isopropyl ether
  6. customThe insoluble solid was removed by filtration
  7. concentrationThe filtrate was concentrated
  8. customtriturated in isopropyl ether
  9. customThe solid was collected
  10. customRecrystallization from acetone-isopropyl ether
  11. customgave a white solid which
  12. customwas dried under vacuum overnight at room temperature to 3.9 g, mp 116°-118° C.

Sources & evidence

ORD record
ord-feca3aaa48ff4182b6f261f19d12a753
Source dataset
uspto-grants-1993_12
Patent number
US05273993

Reaction notes

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