Triethylamine → HCID 67215227, compound

HRID 2421198Notes

Reaction equation

HRID 2421198 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]([OH:15])=O.[S:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]([NH:23][NH2:24])=O.[Cl-].ClC1N(C)C=C[N+]=1C.C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]1[O:15][C:21]([C:17]2[S:16][CH:20]=[CH:19][CH:18]=2)=[N:23][N:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 143435-Methyl-3-phenylisoxazole-4-carboxylic acidHCID 73098Thiophene-2-carbohydrazideHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chloride

Product 1

HCID 67215227HCID 67215227, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-methyl-3-phenylisoxazole-4-carboxylic acid (357 mg, 1.76 mmol) in dichloromethane (7 mL) was added thiophene-2-carboxylic acid hydrazide (250 mg, 1.76 mmol) and 2-chloro-1,3-dimethylimidazolium chloride (654 mg, 3.87 mmol). After the solution was stirred for 15 min at ambient temperature triethylamine (1.2 mL, 8.79 mmol) was added at 0° C. and the light brown suspension was stirred for 18 h while warming to ambient temperature. It was washed with water (25 mL) and aqueous sodium carbonate (half saturated, 25 mL). The aqueous layers were extracted with dichloromethane and the combined organic layers were dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 70:30) afforded the title compound (233 mg, 43%) as a light yellow semisolid. MS: m/e=310.3 [M+H]+.

Workup

  1. additionwas added at 0° C.
  2. washIt was washed with water (25 mL) and aqueous sodium carbonate (half saturated, 25 mL)
  3. extractionThe aqueous layers were extracted with dichloromethane
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-8cc1e6e851ad42d18dee8f836d92ff5c
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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