Triethylamine → HCID 68773176, compound

HRID 1628502Notes

Reaction equation

HRID 1628502 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][C:14]2[C:15]([NH:25][CH2:26][CH2:27][CH2:28][OH:29])=[C:16]([CH:21]=[CH:22][C:23]=2[Cl:24])[C:17]([O:19][CH3:20])=[O:18])=S)=[C:6]([CH3:30])[CH:5]=1)(=[O:3])[NH2:2].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>O1CCCC1.C(=O)([O-])O.[Na+]>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:25]([CH2:26][CH2:27][CH2:28][OH:29])[C:15]3[C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=[C:23]([Cl:24])[C:14]=3[N:13]=2)=[C:6]([CH3:30])[CH:5]=1)(=[O:3])[NH2:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86632894HCID 86632894, compound

Product 1

HCID 68773176HCID 68773176, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the resulting thiourea (2.10 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (981 mg, 5.12 mol), and triethylamine (0.72 mL) in tetrahydrofuran (60 mL) was stirred at 50° C. for 2 hr. The mixture was diluted with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was washed with ethyl acetate to give the title compound as a colorless powder (1.30 g, 3.12 mmol, 39% in 2 steps).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. washThe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-0ac7e834152c48d582d54552e44afd33
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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