Triethylamine → HCID 22144554, compound

HRID 1824800Notes

Reaction equation

HRID 1824800 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([NH2:11])=[C:8]([SH:10])[CH:9]=1.C(N(CC)CC)C.[Br:19][C:20]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](Cl)=O.[OH-].[Na+]>CN1CCCC1=O>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:22]([C:21]3[CH:25]=[CH:26][CH:27]=[C:28]([O:29][CH3:30])[C:20]=3[Br:19])[S:10][C:8]=2[CH:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 22144509HCID 22144509, compoundHCID 221445602-Bromo-3-methoxybenzoyl chloride

Product 1

HCID 22144554HCID 22144554, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

5-Methoxy-2-aminobenzenethiol hydrochloride (83 g, 4.33 mmol) was dissolved in 1-methyl-2-pyrrolidinone (10 mL). After triethylamine (0.60 mL, 4.33 mmol) was added, the mixture was stirred at room temperature for 10 min. 2-Bromo-3-methoxybenzoyl chloride (1.08 g, 4.33 mmol) in 1-methyl-2-pyrrolidinone (10 mL) was then added and the mixture was heated at 100° C. for 40 min. The mixture was cooled to room temperature and 1N NaOH was added to PH 9. The mixture was extracted with ethylacetate and combined ethylacetate were washed with brine, concentrated. After chromatographic purification gave 6-methoxy-2-(2-bromo-3-methoxy-phenyl)-benzothiazole (0.98 g, 65% yield) as a yellow solid. Mass spec: MH+=350.

Workup

  1. temperaturethe mixture was heated at 100° C. for 40 min
  2. temperatureThe mixture was cooled to room temperature
  3. extractionThe mixture was extracted with ethylacetate and combined ethylacetate
  4. washwere washed with brine
  5. concentrationconcentrated
  6. customAfter chromatographic purification

Sources & evidence

ORD record
ord-277e1d16b531404193aaab6758a74ff7
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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