Acetyl chloride → HCID 68524296, compound

HRID 1990099Notes

Reaction equation

HRID 1990099 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.[C:29](Cl)(=[O:31])[CH3:30].[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][C:29](=[O:31])[CH3:30])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 68525996HCID 68525996, compound

Product 1

HCID 68524296HCID 68524296, compoundYield 90%

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 acetyl 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 (0.125 g, yield 90%). MS (ES+, m/e): 361 (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-0cf0eb4c791b4e0aab3bf78b1bc40e1f
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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