Acetyl chloride → HCID 60207425, compound

HRID 1192205Notes

Reaction equation

HRID 1192205 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:25])[C:7]=1[S:8][C:9]1[S:13][C:12]([C:14]([NH:16][CH:17]2[CH2:21][CH2:20][NH:19][CH2:18]2)=[O:15])=[CH:11][C:10]=1[N+:22]([O-:24])=[O:23].[C:26](Cl)(=[O:28])[CH3:27].C(N(CC)CC)C>O1CCCC1>[C:26]([N:19]1[CH2:20][CH2:21][CH:17]([NH:16][C:14]([C:12]2[S:13][C:9]([S:8][C:7]3[C:6]([Cl:25])=[CH:5][N:4]=[CH:3][C:2]=3[Cl:1])=[C:10]([N+:22]([O-:24])=[O:23])[CH:11]=2)=[O:15])[CH2:18]1)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 60207421HCID 60207421, compound

Product 1

HCID 60207425HCID 60207425, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-((3,5-dichloropyridin-4-yl)thio)-4-nitro-N-(pyrrolidin-3-yl)thiophene-2-carboxamide (0.15 g, 0.36 mmol) and acetyl chloride (41.0 mg, 0.54 mmol) in tetrahydrofuran (5.0 mL), was added triethylamine (54.2 mg, 0.54 mmol). The resulting reaction mixture was stirred at ambient temperature for 4 hours. After this time, the reaction mixture was quenched with ice water and stirred at room temperature for 20 minutes and the resulting precipitate was collected by filtration, washed with water (10 mL) and dried in vacuo at 40° C. overnight to afford the title product as an solid (80 mg, 48% yield). 1H NMR (400 MHz, d6-DMSO) δ: 8.98 (2H, m), 8.91 (1H, d), 8.51(1H, m), 3.68 (1H, m), 3.50 (2H, m), 3.23 (2H, m), 2.09 (1H, m), 1.94 (3H, m). MS m/z: 461.17, 363.17 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. customAfter this time, the reaction mixture was quenched with ice water
  3. stirringstirred at room temperature for 20 minutes
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashed with water (10 mL)
  6. customdried in vacuo at 40° C. overnight

Sources & evidence

ORD record
ord-95d572a5b1a742f8b2a8628cc84e7067
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

Loading…