Triethylamine → 4-(2,4-dichlorophenyl)-5-methyl-2-[N-(alpha-cyclopropyl-4-bromobenzyl)-N-propylamino]thiazole

HRID 399629Notes

Reaction equation

Br[CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])=O.[CH:14]1([CH:17]([N:25]([CH2:29][CH2:30][CH3:31])[C:26]([NH2:28])=[S:27])[C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[CH2:16][CH2:15]1.C(N(CC)CC)C>C(O)C>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[C:3]1[N:28]=[C:26]([N:25]([CH:17]([CH:14]2[CH2:16][CH2:15]2)[C:18]2[CH:19]=[CH:20][C:21]([Br:24])=[CH:22][CH:23]=2)[CH2:29][CH2:30][CH3:31])[S:27][C:2]=1[CH3:13]

Participants

Conditions

Temperature: 65 °C

Procedure

14 g of 2-bromo-1-(2,4-dichlorophenyl)-1-propanone (Compound 1), 17.1 g of N-(α-cyclopropyl-4-bromobenzyl)-N-propylthiourea (Compound 64) and 7.6 ml of triethylamine are dissolved in 200 ml of ethanol and the solution is heated to 65° C. The reaction is monitored by TLC. At the end of the reaction, the ethanol is removed and the residue is hydrolysed with water and extracted with methylene chloride. The organic phases are washed and dried. The product is purified on a column of silica, using a mixture of cyclohexane and ethyl acetate (20:1 v/v) as eluent.

Workup

customAt the end of the reaction
customthe ethanol is removed
extractionextracted with methylene chloride
washThe organic phases are washed
customdried
customThe product is purified on a column of silica
additiona mixture of cyclohexane and ethyl acetate (20:1 v/v) as eluent

Sources & evidence

ORD record: ord-41160342b3da4f80b92077bc9f490998
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05821255

Reaction notes

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