Ammonia → HCID 13569205, compound

HRID 745919Notes

Reaction equation

HRID 745919 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.Cl[S:8]([OH:11])(=O)=[O:9].[O:12]([CH2:19][CH2:20][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[NH3:26]>>[S:8]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:19][CH2:20][N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[CH:14][CH:15]=1)(=[O:11])(=[O:9])[NH2:26]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 1356917230170-83-3

Product 1

HCID 13569205HCID 13569205, compound

Conditions

Temperature
0 °C

Procedure

Phosphorus pentachloride (2.08 g) was added cautiously to chlorosulphonic acid (2.91 g) and the resulting solution was cooled to 0° C. 1-(2-Phenoxyethyl)imidazole (1.88 g) was added in portions, allowing the effervescence to subside after each addition. The mixture was heated on a steam bath for 10 minutes, cooled, and poured onto a mixture of crushed ice and excess concentrated ammonia solution. The resulting gummy solid was filtered off, washed with water, sucked as dry as possible at the filter pump and chromatographed on silica gel. Elution with a mixture of chloroform and methanol (4:1) gave a gum which crystallised on trituration with a few mls. of ethanol. The solid was crystallised from ethanol to give 1-[2-(4-sulphamoylphenoxy)ethyl]imidazole (0.5 g), m.p. 147.5°-148.5° C. Found: C, 49.57; H, 4.93; N, 15.36. C11H13N3O3S requires: C, 49.42; H, 4.90; N, 15.72%.

Workup

  1. additionafter each addition
  2. temperatureThe mixture was heated on a steam bath for 10 minutes
  3. temperaturecooled
  4. filtrationThe resulting gummy solid was filtered off
  5. washwashed with water
  6. customas dry as possible at the filter pump
  7. customchromatographed on silica gel
  8. washElution
  9. additionwith a mixture of chloroform and methanol (4:1)
  10. customgave a gum which
  11. customcrystallised on trituration with a few mls
  12. customThe solid was crystallised from ethanol

Sources & evidence

ORD record
ord-23bc9cd4acf24b81acbd8e22236723d7
Source dataset
uspto-grants-1986_07
Patent number
US04602016

Reaction notes

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