Triethylamine → HCID 68524429, compound

HRID 1990100Notes

Reaction equation

HRID 1990100 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:20][CH3:21])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)=[O:5])[CH3:2].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].[NH4+].[Cl-]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([S:20][CH3:21])=[C:9]([C:18]#[N:19])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([NH:17][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 68525996HCID 68525996, compound

Product 1

HCID 68524429HCID 68524429, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 3-(4-Aminophenyl)-4-cyano-5-methylsulfanyl-thiophene-2-carboxylic acid ethyl ester (0.1 g, 1.0 eq) in CH2Cl2 (5 mL) and stir. Add triethylamine (1.5 eq) and methanesulfonyl chloride (1.0 eq) at room temperature. Stir the mixture overnight. Add a saturated solution of NH4Cl and extract with CH2Cl2 (2×50 mL). Dry over NaSO4, filter and evaporate to dryness. Purification by chromatography (hexane:ethyl acetate 4:1) provides the title compound (0.028 g, Yield 25%). MS (ES+, m/e): 397 (M+1).

Workup

  1. customat room temperature
  2. extractionextract with CH2Cl2 (2×50 mL)
  3. dry with materialDry over NaSO4
  4. filtrationfilter
  5. customevaporate to dryness
  6. customPurification by chromatography (hexane:ethyl acetate 4:1)

Sources & evidence

ORD record
ord-2b8893a4da1e4608a4317cf07b1bc068
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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