Toluene → N-(3,5-Bis(hydroxymethyl)phenyl)-1-((3,4-dichlorophenyl)methyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

HRID 450517Notes

Reaction equation

HRID 450517 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:18][C:19]3[CH:20]=[C:21]([C:29](OC)=[O:30])[CH:22]=[C:23]([C:25](OC)=[O:26])[CH:24]=3)=[O:17])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.[NH4+].[Cl-]>C1COCC1>[OH:26][CH2:25][C:23]1[CH:24]=[C:19]([NH:18][C:16]([C:13]2[N:12]=[N:11][N:10]([CH2:9][C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[C:14]=2[CH3:15])=[O:17])[CH:20]=[C:21]([CH2:29][OH:30])[CH:22]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 59583399Dimethyl 5-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-benzenedicarboxylate2×

Product 1

HCID 42603248N-(3,5-Bis(hydroxymethyl)phenyl)-1-((3,4-dichlorophenyl)methyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 5-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-benzenedicarboxylate (Intermediate 14) (0.65 g, 1.3 mmol) in THF (40 mL), was added a 1M solution of DIBAL-H in toluene (10 mL, 7 eq) and the reaction was stirred to room temperature for 2 hours. Solid NH4Cl was added and the reaction mixture was stirred at RT for 30 min. The aqueous phase was extracted with ether and AcOEt, dried over sodium sulphate and evaporated. After recrystallisation from acetonitrile, the title compound was obtained as a white solid (240 mg, 44%). HRMS calculated for C19H18Cl2N4O3 (M+H)+421.0834, found: 421.0833, Rt: 2.51 min. MP: 194.5° C.

Workup

  1. stirringthe reaction mixture was stirred at RT for 30 min
  2. extractionThe aqueous phase was extracted with ether and AcOEt
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customAfter recrystallisation from acetonitrile

Sources & evidence

ORD record
ord-3ffd94480ee24ac083d22caaed5c36e2
Source dataset
uspto-grants-2013_07
Patent number
US08486977B2

Reaction notes

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