Triethylamine → HCID 11778574, compound

HRID 1819747Notes

Reaction equation

HRID 1819747 reaction equation
[OH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.CCN(CC)CC.Br[CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)=[O:21]>C1COCC1>[O:21]=[C:20]([C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)[CH2:19][N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 692722-Bromo-4'-methylacetophenoneHCID 178517143HCID 178517143, compound

Product 1

HCID 11778574HCID 11778574, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-hydroxybenzothiazole (1.17 g, 7.58 mmol) in THF (10 mL) was added Et3N (1.1 mL, 7.89 mmol). A solution of 2-bromo-4′-methylacetophenone (1.67 g, 7.06 mmol) in THf (10 mL) was added dropwise. Another equivalent of Et3N was added after 24 hours. Purification by flash chromatography on silicagel (CH2Cl2) gave a white powder in 67% yield: mp 168-170° C.; 1H-NMR (DMSO-d6) 2.43 (s, 3H), 5.62 (s, 2H), 7.21 (t, 1H), 7.27 (d, 1H) 7.32 (t, 1H), 7.42 (d, 2H), 7.70 (d, 1H), 8.01 (d, 2H); Anal. (C16H13NO2S) C, H, N.

Workup

  1. customPurification by flash chromatography on silicagel (CH2Cl2)
  2. customgave a white powder in 67% yield

Sources & evidence

ORD record
ord-ece1c7ab6d9146b789e42fa7d54eb489
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

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