Water → HCID 69287896, compound

HRID 2222195Notes

Reaction equation

HRID 2222195 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[S:13][C:14]([CH3:20])=[C:15]([C:17]([OH:19])=[O:18])[N:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25].CCN(CC)CC.O>C(Cl)Cl>[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:23]=1[C:24]([N:11]([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:12]1[S:13][C:14]([CH3:20])=[C:15]([C:17]([OH:19])=[O:18])[N:16]=1)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 86056604HCID 86056604, compound

Product 1

HCID 69287896HCID 69287896, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2.74 g (9.3 mmol) 2-(3,4-Dimethoxy-phenylamino)-5-methyl-thiazole-4-carboxylic acid, 1.95 ml (14 mmol) 2,4-Dichlorobenzoyl chloride and 3.88 ml (27.9 mmol) NEt3 in 30 ml DCM was stirred at room temperature for 5 min and 50 ml water was added and the mixture was stirred at room temperature for 16 h. After removal of all volatiles the residue was extracted with DCM and evaporated under reduced pressure to yield 4.18 g of amorphous light brown solid which was used without further purification in the consecutive step. MS (m/e): 467.2 (MH+, 100%)

Workup

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. customAfter removal of all volatiles the residue
  3. extractionwas extracted with DCM
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2a6410ad81eb4accacaac96656a26800
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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