Triethylamine → HCID 57813606, compound

HRID 1941969Notes

Reaction equation

HRID 1941969 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:10]3[S:14][C:13]([NH2:15])=[N:12][C:11]=3[CH:16]=2)[CH:2]=1.C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>C1(C)C=CC=CC=1>[CH2:34]([O:33][C:31](=[O:32])[NH:15][C:13]1[S:14][C:10]2[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:8][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:16][C:11]=2[N:12]=1)[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 57813721HCID 57813721, compound

Product 1

HCID 57813606HCID 57813606, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 5-pyridin-3-yl-7-pyridin-2-yl-benzothiazol-2-ylamine (0.10 g, 0.33 mmol) in toluene (5 mL) was added triethylamine (0.10 ml, 0.07 mmol) at room temperature. The reaction mixture was heated to 40° C. followed by the addition of ethyl chloroformate (0.17 g, 0.16 mmol). The resulting reaction mixture was stirred under nitrogen atmosphere at 70° C. for 16 h. After the completion of reaction (TLC monitoring) toluene was evaporated under reduced pressure. The crude solid residue was washed with water and was purified by chromatography over silica gel (230-400 M) using ethyl acetate:hexane (60:40) to provide the title compound as white solid (0.046 g, 38%). M.P. 235° C.

Workup

  1. customThe resulting reaction mixture
  2. customwas evaporated under reduced pressure
  3. washThe crude solid residue was washed with water
  4. customwas purified by chromatography over silica gel (230-400 M)

Sources & evidence

ORD record
ord-f46aa71a6c124b61990d3a5ee5aabc63
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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