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Triethylamine → HCID 42633832, compound

HRID 1009056
Notes
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Reaction equation

HRID 1009056 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[N:35]=[C:36]([NH2:41])[S:37][C:38]=1[S:39][CH3:40])[CH3:33]>C(#N)C>[CH2:32]([C:34]1[N:35]=[C:36]([NH:41][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])[S:37][C:38]=1[S:39][CH3:40])[CH3:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 67274431HCID 67274431, compoundHCID 86630962HCID 86630962, compound

Product 1

HCID 42633832HCID 42633832, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
60 °C

Procedure

5-(2-Methoxy-ethyl)-4-methyl-thiophene-2-sulfonic acid amide (0.235 g, 1.00 mmol) was dissolved in 6 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.157 g, 1.00 eq.) and triethylamine (0.348 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1. h. The above prepared 4-ethyl-5-methylsulfanyl-thiazol-2-ylamine (0.211 g, 1.00 eq. as hydrochloride) was then added, and the mixture heated to 60° C. over night. Cooling, pouring onto crashed ice, twofold extraction with ethyl acetate, washing with brine, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, ethyl acetate/MeOH=95/5) and trituration over heptane yielded 0.296 g of the title compound as light brown solid.

Workup

  1. customkept at ambient temperature for 1
  2. additionwas then added
  3. temperatureCooling
  4. additionpouring
  5. extractionice, twofold extraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-119f63ccebb6416d9dc9da17a48aedd5
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07973051B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes