Thiourea → HCID 22270379, compound

HRID 488593Notes

Reaction equation

HRID 488593 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[C:9]([NH:12]C(=O)CCl)([CH3:11])[CH3:10])=[CH:4][CH:3]=1.NC(N)=S>C(O)C.C(O)(=O)C>[ClH:1].[NH2:12][C:9]([CH3:11])([CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=1)[CH3:10]

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 22270723HCID 22270723, compound

Product 1

HCID 22270379HCID 22270379, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N-[2,3-bis(4-chlorophenyl)-1,1-dimethylpropyl]chloroacetamide (Step C, 1.3 g, 3.8 mmol) in ethanol (10 mL) and acetic acid (2 mL) was added thiourea (0.34 g, 4.5 mmol). The reaction was stirred at 80° C. overnight to give a white precipitate. The precipitate was removed by filtration and washed with ethanol (10 mL), and the filtrate was diluted with dilute aqueous sodium hydroxide and extracted with hexane (2×50 mL). The combined extracts were dried over sodium hydroxide, filtered, and concentrated to dryness, and the residue was taken up by hydrogen chloride in dioxane (4 M, 5 mL) and concentrated to dryness to give the title compound. 1H NMR (500 MHz, CD3OD): (free amine) δ 7.22-7.14 (m, 4H), 7.06 (d, 2H), 6.96 (d, 2H), 3.22 (dd, 1H), 2.95 (dd, 1H), 2.86 (dd, 1H), 1.16 (s, 3H), 1.10 (s, 3H).

Workup

  1. customto give a white precipitate
  2. customThe precipitate was removed by filtration
  3. washwashed with ethanol (10 mL)
  4. additionthe filtrate was diluted with dilute aqueous sodium hydroxide
  5. extractionextracted with hexane (2×50 mL)
  6. dry with materialThe combined extracts were dried over sodium hydroxide
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3dac4017265e4bcf8fb431f9bacfebba
Source dataset
uspto-grants-2005_12
Patent number
US06972295B2

Reaction notes

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