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Triethylamine → 3-{3-[2-(2,4-Di-tert-amylphenoxy)butyramido]-benzamido}-5-butanoyloxy-1-(2,4,6-trichlorophenyl)-4-(1-pyrazolyl)-1H-pyrazole

HRID 1660540
Notes
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Reaction equation

HRID 1660540 reaction equation
[C:1]([C:6]1[CH:47]=[C:46]([C:48]([CH2:51][CH3:52])([CH3:50])[CH3:49])[CH:45]=[CH:44][C:7]=1[O:8][CH:9]([CH2:42][CH3:43])[C:10]([NH:12][C:13]1[CH:14]=[C:15]([CH:39]=[CH:40][CH:41]=1)[C:16]([NH:18][C:19]1[CH:23]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)[C:22](=[O:29])[N:21]([C:30]2[C:35]([Cl:36])=[CH:34][C:33]([Cl:37])=[CH:32][C:31]=2[Cl:38])[N:20]=1)=[O:17])=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:60](OCl)(=[O:64])[CH2:61][CH2:62][CH3:63].C(OCC)(=O)C>O1CCCC1>[C:1]([C:6]1[CH:47]=[C:46]([C:48]([CH2:51][CH3:52])([CH3:49])[CH3:50])[CH:45]=[CH:44][C:7]=1[O:8][CH:9]([CH2:42][CH3:43])[C:10]([NH:12][C:13]1[CH:14]=[C:15]([CH:39]=[CH:40][CH:41]=1)[C:16]([NH:18][C:19]1[C:23]([N:24]2[CH:28]=[CH:27][CH:26]=[N:25]2)=[C:22]([O:29][C:60](=[O:64])[CH2:61][CH2:62][CH3:63])[N:21]([C:30]2[C:31]([Cl:38])=[CH:32][C:33]([Cl:37])=[CH:34][C:35]=2[Cl:36])[N:20]=1)=[O:17])=[O:11])([CH2:4][CH3:5])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 136682733-{3-[2-(2,4-Di-tert-amylphenoxy)butyramido]benzamido}-1-(2,4,6-trichlorophenyl)-4-(1-pyrazolyl)-5-oxo-2-pyrazolineHCID 18444075Butanoyloxy chloride

Product 1

HCID 205569513-{3-[2-(2,4-Di-tert-amylphenoxy)butyramido]-benzamido}-5-butanoyloxy-1-(2,4,6-trichlorophenyl)-4-(1-pyrazolyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

30.6 g of 3-{3-[2-(2,4-di-tert-amylphenoxy)butyramido]benzamido}-1-(2,4,6-trichlorophenyl)-4-(1-pyrazolyl)-5-oxo-2-pyrazoline (prepared by the method described in German Patent Application (OLS) No. 2,536,191) was dissolved in 100 ml of tetrahydrofuran and 5 g of triethylamine was added. To the solution, a solution containing 3.5 g of butanoyloxy chloride dissolved in 10 ml of tetrahydrofuran was dropwise added. After the addition of the solution, the mixture was stirred for 1 hour. 500 ml of ethyl acetate was added to the reaction mixture and washed several times with water. The oil layer was dried with anhydrous sodium sulfate and concentrated. Upon crystallization of the residue from acetonitrile, 24 g of Coupler (5) was obtained. The melting point of the coupler was 63° to 68° C.

Workup

  1. additionwas dropwise added
  2. additionAfter the addition of the solution
  3. washwashed several times with water
  4. dry with materialThe oil layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customUpon crystallization of the residue from acetonitrile, 24 g of Coupler (5)
  7. customwas obtained
  8. customwas 63° to 68° C.

Sources & evidence

ORD record
ord-b3fad9f1cffc42d2ba9d9de60a7fb7f4
Source dataset
uspto-grants-1981_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04308343

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes