Triethylamine → HCID 68772550, compound

HRID 1628551Notes

Reaction equation

HRID 1628551 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:3]=1[NH:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=S.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O1CCCC1.C(OCC)(=O)C>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[NH:17][C:15]1[NH:14][C:3]2[C:4]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[N:1]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86632909HCID 86632909, compound

Product 1

HCID 68772550HCID 68772550, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-[2-amino-6-(diethylamino)-3-fluorophenyl]-3-(2,4-dichlorophenyl)thiourea (300 mg, 0.748 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (151 mg, 0.788 mmol) and triethylamine (0.115 mL, 0.825 mmol) in tetrahydrofuran (3 mL) was stirred at 50° C. for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 25% ethyl acetate/n-hexane mixture to give the title compound as a colorless solid (191 mg, 0.521 mmol, 70%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 25% ethyl acetate/n-hexane mixture

Sources & evidence

ORD record
ord-c318d76531f545ef83072da776381e07
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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