Dimethylformamide → HCID 73299960, compound

HRID 1094936Notes

Reaction equation

HRID 1094936 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[C:5]([NH:7][CH2:8][CH2:9][C:10](=[O:12])[NH2:11])=[O:6].CN(C)C=O.[C:21](N1C=CN=C1)(N1C=CN=C1)=[S:22].[N:33](=[C:35]([C:37]1[C:41]([OH:42])=[C:40]([C:43]2[CH:48]=[CH:47][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:45][CH:44]=2)[N:39]([CH3:53])[N:38]=1)[CH3:36])[NH2:34]>O>[C:10]([CH2:9][CH2:8][NH:7][C:5](=[O:6])[C:4]1[CH:13]=[CH:14][CH:15]=[C:2]([NH:1][C:21]([NH:34][N:33]=[C:35]([C:37]2[C:41]([OH:42])=[C:40]([C:43]3[CH:44]=[CH:45][C:46]([C:49]([F:52])([F:51])[F:50])=[CH:47][CH:48]=3)[N:39]([CH3:53])[N:38]=2)[CH3:36])=[S:22])[CH:3]=1)(=[O:12])[NH2:11]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 802641,1'-ThiocarbonyldiimidazoleHCID 22567500HCID 22567500, compoundHCID 723601133-(1-hydrazonoethyl)-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-ol

Product 1

HCID 73299960HCID 73299960, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Amino-N-(2-carbamoylethyl)benzamide (56 mg, 0.27 mmol) was stirred with a dimethylformamide solution of thiocarbonyldiimidazole (0.1 M, 2.25 mL, 0.225 mmol) at room temperature for 1.5 hours, and then with a dimethylformamide solution of 3-(1-hydrazonoethyl)-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-ol prepared in Reference Synthetic Example 14 (0.1 M, 1.8 mL, 0.18 mmol) at 40° C. for 1 hour, and then stirred at room temperature for 17 hours. After addition of water and saturated aqueous sodium chlorides the solution was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated, and chloroform and hexane were added to the residue. The precipitated solid was collected by filtration, washed with hexane and dried to give 102.7 mg of the desired product (yield 100%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated
  5. additionchloroform and hexane were added to the residue
  6. filtrationThe precipitated solid was collected by filtration
  7. washwashed with hexane
  8. customdried

Sources & evidence

ORD record
ord-04b6e6d46024437f8a2a135594c1ee36
Source dataset
uspto-grants-2012_03
Patent number
US08134013B2

Reaction notes

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