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Triethylamine → N-[(5-bromo-4-ethyl-1,3-thiazol-2-yl)carbamoyl]-5-methylthiophene-3-sulfonamide

HRID 1009027
Notes
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Reaction equation

HRID 1009027 reaction equation
[CH3:1][C:2]1[S:6][CH:5]=[C:4]([S:7]([NH2:10])(=[O:9])=[O:8])[CH:3]=1.Cl[C:12](OC1C=CC=CC=1)=[O:13].C(N(CC)CC)C.[Br:28][C:29]1[S:33][C:32]([NH2:34])=[N:31][C:30]=1[CH2:35][CH3:36]>C(#N)C>[Br:28][C:29]1[S:33][C:32]([NH:34][C:12]([NH:10][S:7]([C:4]2[CH:3]=[C:2]([CH3:1])[S:6][CH:5]=2)(=[O:9])=[O:8])=[O:13])=[N:31][C:30]=1[CH2:35][CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 572350435-Methylthiophene-3-sulfonamideHCID 665201935-Bromo-4-ethylthiazol-2-amine

Product 1

HCID 42633277N-[(5-bromo-4-ethyl-1,3-thiazol-2-yl)carbamoyl]-5-methylthiophene-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent
2×

Conditions

Temperature
57.5 °C

Procedure

5-Methyl-thiophene-3-sulfonic acid amide (0.0496 g, 0.28 mmol) was dissolved in 1.5 mL of abs. acetonitrile and treated successively with phenyl chloroformate (0.0443 g, 1.01 eq.) and triethylamine (0.097 mL, 2.5 eq.), and the mixture kept at ambient temperature for 1.25 h. The above prepared 5-bromo-4-ethyl-thiazol-2-ylamine (0.061 g, 1.05 eq.), dissolved in a tiny amount of acetonitrile, was then added, and the mixture heated to 55-60° C. over night. Cooling, pouring onto crashed ice/NH4Cl, twofold extraction with ethyl acetate, washing with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, MeOH/ethyl acetate=1/99), yielded eventually, after precipitation from ethyl acetate/heptane, 0.038 g of the title compound as off-white solid.

Workup

  1. additionwas then added
  2. temperatureCooling
  3. additionpouring
  4. extractionice/NH4Cl, twofold extraction with ethyl acetate
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents
  7. customyielded eventually
  8. customafter precipitation from ethyl acetate/heptane, 0.038 g of the title compound as off-white solid

Sources & evidence

ORD record
ord-eb8ee93d08944e4b9b6115fc7395764f
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