Hydrazine hydrate (1:1) → HCID 58986237, compound

HRID 12605Notes

Reaction equation

HRID 12605 reaction equation
O.[NH2:2][NH2:3].Br[CH:5]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)[CH2:6][CH2:7][CH3:8]>C(O)(C)C>[F:16][C:15]([F:18])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([CH:5]([NH:2][NH2:3])[CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 687136191-(1-Bromobutyl)-4-(trifluoromethyl)benzene

Product 1

HCID 58986237HCID 58986237, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Hydrazine monohydrate (8.9 g) was dissolved in isopropanol (25 ml) and 1-(1-bromobutyl)-4-(trifluoromethyl)benzene (as prepared in WO 2005013985, 2.0 g, 7.12 mmol) added. The mixture was heated to 70° C. and stirred for 16 h. After this time the solvent was removed and the residue taken up in ethyl acetate and washed three times (H2O). The combined organics were dried (sodium sulfate) and concentrated to give the mixture of products as a white solid suspended in a clear oil. The mixture was triturated with diethyl ether to give a white solid; 1H NMR δ (ppm)(DMSO): 9.20 (1 H, s), 7.76 (2 H, d, J=8.1 Hz), 7.64 (2 H, s), 4.16 (1 H, s), 1.85 (1 H, s), 1.59 (1 H, s), 1.20-0.96 (2 H, m), 0.82 (3 H, t, J=7.3 Hz).

Workup

  1. customAfter this time the solvent was removed
  2. washwashed three times (H2O)
  3. dry with materialThe combined organics were dried (sodium sulfate)
  4. concentrationconcentrated
  5. customto give
  6. additionthe mixture of products as a white solid
  7. customThe mixture was triturated with diethyl ether
  8. customto give a white solid

Sources & evidence

ORD record
ord-7c2786f87aa442578313278254796421
Source dataset
uspto-grants-2010_06
Patent number
US07728022B2

Reaction notes

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