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Benzyl Bromide → 2-(Benzyloxycarbonyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 463977
Notes
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Reaction equation

HRID 463977 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:10]([NH:12][S:13]([C:16]2[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=2[C:18]([OH:20])=[O:19])(=[O:15])=[O:14])=[O:11])[N:3]=1.C(N(CC)CC)C.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O1CCCC1>[CH2:32]([O:19][C:18]([C:17]1[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=1[S:13]([NH:12][C:10]([NH:9][C:4]1[N:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[N:3]=1)=[O:11])(=[O:15])=[O:14])=[O:20])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 52998Sulfometuron

Product 1

HCID 131765802-(Benzyloxycarbonyl)-N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 1.75 g of 2-(4,6-dimethylpyrimidin-2-ylaminocarbonylsulfamoyl)benzoic acid was added 0.51 g of triethylamine in 10 ml tetrahydrofuran and 0.88 g of benzyl bromide in 10 ml of tetrahydrofuran. The mixture was heated to reflux for 1.5 hours, filtered and the tetrahydrofuran evaporated in-vacuo. The residue was extracted with hot 1-chlorobutane, diluted with ethyl acetate, washed with water and saturated aqueous sodium bicarbonate. The organic phase was dried over magnesium sulfate, filtered and the solvents evaporated in-vacuo. The resultant residue was crystallized from 1-chlorobutane to a melting point of 157°. This product showed absorption peaks in the infrared region at 1720, 1600, 1560 cm-1 consistent for the desired ester and absorption by nuclear magnetic resonance at 2.45', singlet, for CH3 ; 5.3δ singlet, CH2 on benzyl; 6.65' singlet CH of pyrimidine and aryl peaks at 7-8δ.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 hours
  3. filtrationfiltered
  4. customthe tetrahydrofuran evaporated in-vacuo
  5. extractionThe residue was extracted with hot 1-chlorobutane
  6. additiondiluted with ethyl acetate
  7. washwashed with water and saturated aqueous sodium bicarbonate
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvents evaporated in-vacuo
  11. customThe resultant residue was crystallized from 1-chlorobutane to a melting point of 157°
  12. customabsorption peaks in the infrared region at 1720, 1600, 1560 cm-1
  13. customconsistent for the desired ester and absorption by nuclear magnetic resonance at 2.45', singlet

Sources & evidence

ORD record
ord-9c145cfb475f4b4cb9b9f1cc96c1fd9a
Source dataset
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04545808

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes