Triethylamine → HCID 67215227, compound

HRID 1983185Notes

Reaction equation

HRID 1983185 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-6770de3f11ec4f6c8bfb4a633f66ba45
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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