Triethylamine → HCID 42633280, compound

HRID 1009036Notes

Reaction equation

HRID 1009036 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[S:9][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:7][C:6]=1[CH3:14].Cl[C:16](OC1C=CC=CC=1)=[O:17].C(N(CC)CC)C.[CH2:32]([C:34]1[S:38][C:37]([NH2:39])=[N:36][C:35]=1[CH3:40])[CH3:33]>C(#N)C>[CH2:32]([C:34]1[S:38][C:37]([NH:39][C:16]([NH:13][S:10]([C:8]2[S:9][C:5]([CH2:4][CH2:3][O:2][CH3:1])=[C:6]([CH3:14])[CH:7]=2)(=[O:12])=[O:11])=[O:17])=[N:36][C:35]=1[CH3:40])[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 127359565-Ethyl-4-methylthiazol-2-amineHCID 67274431HCID 67274431, compound

Product 1

HCID 42633280HCID 42633280, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

5-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonic acid amide (0.1556 g, 0.661 mmol) was dissolved in 4 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.103 g, 1.00 eq.) and triethylamine (0.229 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1 h. The above prepared 5-ethyl-4-methyl-thiazol-2-ylamine (0.094 g, 1.00 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with brine, drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, ethyl acetate), yielded eventually 0.089 g of the title compound as light brown solid.

Workup

  1. additionwas then added
  2. temperatureCooling
  3. additionpouring
  4. extractionice/NH4Cl, twofold extraction with ethyl acetate
  5. washwashing with brine
  6. dry with materialdrying over magnesium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-e5944f0881a4462b8ecb4ae049f4815d
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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