Sodium hydride → 4-(2,4-dichlorophenyl)-5-methyl-2-[N-(alpha-methylbenzyl)-N-(cyclopropylmethyl)amino]thiazole

HRID 128694Notes

Reaction equation

HRID 128694 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([NH:15][CH:16]([CH3:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:12][C:13]=1[CH3:14].BrC(C)C([C:28]1[CH:33]=[CH:32][C:31](Cl)=CC=1Cl)=O.[H-].[Na+]>O1CCCC1.C1(CBr)CC1.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([N:15]([CH:16]([CH3:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:31][CH:32]2[CH2:28][CH2:33]2)[S:12][C:13]=1[CH3:14]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 109239912-Bromo-1-(2,4-dichlorophenyl)propan-1-oneHCID 193748634-(2,4-dichlorophenyl)-5-methyl-2-[N-(alpha-methylbenzyl)amino]thiazole

Product 1

HCID 193748504-(2,4-dichlorophenyl)-5-methyl-2-[N-(alpha-methylbenzyl)-N-(cyclopropylmethyl)amino]thiazole

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 81503BromomethylcyclopropaneSolvent

Procedure

At 0° C., add 0.5 g of 4-(2,4-dichlorophenyl)-5-methyl-2-[N-(α-methylbenzyl)amino]thiazole (prepared from Compound 92 and Compound 15 according to the process described in Example 1), dissolved in 5 ml of anhydrous tetrahydrofuran, and 66 mg of sodium hydride. After 30 minutes of stirring at room temperature, run in 0.67 ml of cyclopropylmethyl bromide dropwise. Leave for eight hours under reflux, cool and dilute the reaction medium with methylene chloride, then pour it onto ice.

Workup

  1. customLeave for eight hours
  2. temperatureunder reflux
  3. temperaturecool
  4. additionpour it onto ice

Sources & evidence

ORD record
ord-3582406116dd456cb4435c34ea56e06e
Source dataset
uspto-grants-1995_11
Patent number
US05464847

Reaction notes

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