Hydrochloric Acid → 3-fluoro-N-(5-ureidomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide

HRID 492089Notes

Reaction equation

HRID 492089 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)(=[O:16])=[O:15])[CH:6]=[CH:5][C:4]1=2.Cl.[O-:25][C:26]#[N:27].[K+]>O>[F:23][C:19]1[CH:18]=[C:17]([S:14]([NH:13][C:7]2[CH:6]=[CH:5][C:4]3[CH:3]([CH2:2][NH:1][C:26]([NH2:27])=[O:25])[CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 57678960N-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-fluoro-benzenesulfonamide

Product 1

HCID 576789793-fluoro-N-(5-ureidomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.23 grams (0.688 mmoles) N-(5-aminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-3-fluoro-benzenesulfonamide, 0.15 mL 6M hydrochloric acid, and 0.112 grams (1.38 mmole) potassium cyanate in 25 mL water was heated under reflux for 1.5 hours. The solid precipitate was collected by filtration and dried in vacuo to provide 3-fluoro-N-(5-ureidomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide as a white solid, 0.21 gram (81%), m.p. 162-163° C., M+H=378.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. filtrationThe solid precipitate was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-e879d5e2b857428fb7e1f38e0efafb16
Source dataset
uspto-grants-2009_05
Patent number
US07531577B2

Reaction notes

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