Hydrogen Bromide → HCID 69286943, compound

HRID 2222187Notes

Reaction equation

HRID 2222187 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[S:9][CH:10]=1)=[O:5])[CH3:2].Br.[Cl:20][C:21]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:11]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:21]=2[Cl:20])[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 53428670Ethyl 2-(4-chloroanilino)-1,3-thiazole-4-carboxylate

Product 1

HCID 69286943HCID 69286943, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.58 g (7.1 mmol) 2-(4-Chloro-phenylamino)-thiazole-4-carboxylic acid ethyl ester; hydrobromide, 2.24 g (10.7 mmol) 2,4-Dichlorobenzoyl chloride and 2.96 ml (21.4 mmol) NEt3 in 30 ml DCM was stirred at room temperature for 24 h. After evaporation of the volatiles the residue was taken up in MeOH and purified with flash column chromatography on silica eluting with a gradient of heptane/ethyl acetate to yield after evaporation of the product fractions 2.81 g (87%) of the title compound. MS (m/e): 457.1 (MH+, 100%)

Workup

  1. customAfter evaporation of the volatiles the residue
  2. custompurified with flash column chromatography on silica eluting with a gradient of heptane/ethyl acetate
  3. customto yield
  4. customafter evaporation of the product fractions 2.81 g (87%) of the title compound

Sources & evidence

ORD record
ord-7e28a14aad3e460ba17d803dc86025e8
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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