Triethylamine → HCID 178486154, compound

HRID 1011503Notes

Reaction equation

HRID 1011503 reaction equation
[NH:1]1[CH:5]=[C:4]([S:6](Cl)(=[O:8])=[O:7])[N:3]=[CH:2]1.Cl.[CH3:11][NH:12][CH3:13].C(N(CC)CC)C>ClCCl>[CH3:11][N:12]([CH3:13])[S:6]([C:4]1[N:3]=[CH:2][NH:1][CH:5]=1)(=[O:8])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 178527435HCID 178527435, compound

Product 1

HCID 178486154HCID 178486154, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1H-imidazole-4-sulfonyl chloride (0.5 g, 3.0 mmol; Matrix Scientific, Columbia, S.C.) in dichloromethane (10 mL) was added dimethylamine hydrochloride (0.245 g, 3.0 mmol) and triethylamine (1.3 mL, 9.0 mmol) at room temperature. The mixture was stirred for 16 hours at room temperature. TLC (petroleum ether/ethyl acetate=0:1) indicated the reaction was complete. The reaction mixture was washed with aq. ammonium chloride (30 mL) and extracted with dichloromethane: methanol=4:1 (3×50 mL). The combined organic phases were concentrated and precipitated from methanol to afford (I-35a) (0.36 g, 68.2%) as a white solid; 1H NMR (400 MHz, CD3OD): δ 7.74 (1H), 7.61 (1H), 2.68 (6H).

Workup

  1. washThe reaction mixture was washed with aq. ammonium chloride (30 mL)
  2. extractionextracted with dichloromethane
  3. concentrationThe combined organic phases were concentrated
  4. customprecipitated from methanol
  5. customto afford (I-35a) (0.36 g, 68.2%) as a white solid

Sources & evidence

ORD record
ord-073e4e513f0c4947bd13e854ead963db
Source dataset
uspto-grants-2011_07
Patent number
US07977367B2

Reaction notes

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