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Methyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate → HCID 15029431, compound

HRID 1588455
Notes
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Reaction equation

HRID 1588455 reaction equation
C[Al](C)C.[N:5]1([S:10]([CH:13]([S:15]([NH2:18])(=[O:17])=[O:16])[CH3:14])(=[O:12])=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1.[CH3:19][O:20][C:21]1[N:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH:28][C:29](=O)[O:30]C)[N:22]=1>C1(C)C=CC=CC=1.ClCCl>[CH3:19][O:20][C:21]1[N:26]=[C:25]([CH3:27])[N:24]=[C:23]([NH:28][C:29](=[O:30])[NH:18][S:15]([CH:13]([S:10]([N:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)(=[O:11])=[O:12])[CH3:14])(=[O:17])=[O:16])[N:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 14404501Methyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamateHCID 15029429HCID 15029429, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 15029431HCID 15029431, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 6344
Dichloromethane
Solvent
2×

Procedure

9 ml (0.018 mol) of a 2M solution of trimethylaluminum in toluene are added dropwise at room temperature to 3.6 g (0.015 mol) of 1-pyrrolidinosulfonylethanesulfonamide (Example 1a) in 150 ml of dichloromethane. When the evolution of gas has ceased, 3.6 g (0.018 mol) of methyl 4-methoxy-6-methyl-1,3,5-triazin-2-ylcarbamate in 30 ml of dichloromethane are added dropwise, and the resulting solution is refluxed for 24 hours. It is cooled and poured into 150 ml of ice-cold 1N hydrochloric acid. The organic phase is separated off, and the water phase is extracted twice with dichloromethane. The organic phase is dried and evaporated. After the crude product has been triturated with diethyl ether, 2.9 g (47% of theory) of 3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-1-(1-pyrrolidinosulfonylethylsulfonyl)urea of melting point 136°-137° C. are obtained.

Workup

  1. temperaturethe resulting solution is refluxed for 24 hours
  2. temperatureIt is cooled
  3. customThe organic phase is separated off
  4. extractionthe water phase is extracted twice with dichloromethane
  5. customThe organic phase is dried
  6. customevaporated
  7. customAfter the crude product has been triturated with diethyl ether, 2.9 g (47% of theory) of 3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-1-(1-pyrrolidinosulfonylethylsulfonyl)urea of melting point 136°-137° C.
  8. customare obtained

Sources & evidence

ORD record
ord-f0b572fbc6fd44e68538dda552923942
Source dataset
uspto-grants-1993_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05223017

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes