Triethylamine → HCID 178490652, compound

HRID 1037943Notes

Reaction equation

HRID 1037943 reaction equation
[C:1]([C:5]1[S:9][C:8](=[NH:10])[NH:7][C:6]=1[CH3:11])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:19][C:20]1[CH:21]=[CH:22][C:23]([O:29][CH3:30])=[C:24]([CH:28]=1)[C:25](Cl)=[O:26]>O1CCCC1>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:25](=[O:26])[C:24]2[CH:28]=[C:20]([Cl:19])[CH:21]=[CH:22][C:23]=2[O:29][CH3:30])/[NH:7][C:6]=1[CH3:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123841765-Chloro-2-methoxybenzoyl chlorideHCID 178433698HCID 178433698, compound

Product 1

HCID 178490652HCID 178490652, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-tert-butyl-4-methylthiazol-2(3H)-imine (250 mg, 1.5 mmol) in tetrahydrofuran (10 mL) was treated with triethylamine (0.25 mL, 1.8 mmol) and 5-chloro-2-methoxybenzoylchloride (307 mg, 1.5 mmol). The reaction mixture was stirred at 60° C. for 18 hours then concentrated under, reduced pressure. The residue was diluted with ethyl acetate and H2O. The organic extract was dried over MgSO4, filtered, concentrated under reduced pressure and dried under vacuum to afford the title compound (490 mg, 96% yield). MS (ESI) m/z 339 (M+H)+.

Workup

  1. concentrationthen concentrated under, reduced pressure
  2. additionThe residue was diluted with ethyl acetate and H2O
  3. extractionThe organic extract
  4. dry with materialwas dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customdried under vacuum

Sources & evidence

ORD record
ord-57053e7075ee4589967e80fb37fbc19d
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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