Dimethylformamide → 7-(2-{1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidene}hydrazinecarbothioamido)-4H-benzo[1,4]oxazin-3-one

HRID 1094939Notes

Reaction equation

HRID 1094939 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]2[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=2[CH:3]=1.CN(C)C=O.[C:18](N1C=CN=C1)(N1C=CN=C1)=[S:19].[N:30](=[C:32]([C:34]1[C:38]([OH:39])=[C:37]([C:40]2[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=2)[N:36]([CH3:50])[N:35]=1)[CH3:33])[NH2:31]>O>[OH:39][C:38]1[C:34]([C:32](=[N:30][NH:31][C:18](=[S:19])[NH:1][C:2]2[CH:12]=[CH:11][C:5]3[NH:6][C:7](=[O:10])[CH2:8][O:9][C:4]=3[CH:3]=2)[CH3:33])=[N:35][N:36]([CH3:50])[C:37]=1[C:40]1[CH:41]=[CH:42][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 802641,1'-ThiocarbonyldiimidazoleHCID 27641827-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 723601133-(1-hydrazonoethyl)-1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-ol

Product 1

HCID 765977637-(2-{1-[4-Hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethylidene}hydrazinecarbothioamido)-4H-benzo[1,4]oxazin-3-oneYield 49%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

7-Amino-4H-benzo[1,4]oxazin-3-one (33 mg, 0.203 mmol) was stirred with a dimethylformamide solution of thiocarbonyldiimidazole (0.1 M, 2.03 mL, 0.203 mmol) at room temperature for 1 hour 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, 1.36 mL, 0.135 mmol) at room temperature for 4 hours Water was added, and the precipitated solid was collected by filtration, washed with water and dried. After addition of chloroform, the solid was collected by filtration washed with chloroform and dried to give 33.6 mg of the desired product (yield 49%).

Workup

  1. additionwas added
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. additionAfter addition of chloroform
  6. filtrationthe solid was collected by filtration
  7. washwashed with chloroform
  8. customdried

Sources & evidence

ORD record
ord-c77f0600e5e24a03bf3250106be82b89
Source dataset
uspto-grants-2012_03
Patent number
US08134013B2

Reaction notes

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