Acetyl chloride → HCID 9943836, compound

HRID 2086919Notes

Reaction equation

HRID 2086919 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([C:13]1[O:14][CH:15]=[CH:16][CH:17]=1)=[O:12].C(N(CC)CC)C.[C:25](Cl)(=[O:27])[CH3:26]>ClCCl>[O:14]1[CH:15]=[CH:16][CH:17]=[C:13]1[C:11]([C:3]1[C:4]2[CH2:10][CH2:9][CH2:8][CH2:7][C:5]=2[S:6][C:2]=1[NH:1][C:25](=[O:27])[CH3:26])=[O:12]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 9856285HCID 9856285, compound

Product 1

HCID 9943836HCID 9943836, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-furan-2-yl-methanone (Example 4, 200 mg, 0.8 mmol) in dichloromethane (5 mL), cooled to 4° C. with an ice-water bath, was added triethylamine (0.12 mL, 0.88 mmol), followed by acetyl chloride (0.062 mL, 0.88 mmol). The mixture was warmed to room temperature, stirred for 12 hours, diluted with dichloromethane (5 mL), and washed with 5% aqueous HCl (5 mL), followed by saturated aqueous NaHCO3 (5 mL). The organic phase was dried (Na2SO4), filtered, and evaporated, and the residue precipitated with ethyl acetate and petroleum ether. Yield: 69%; IR (KBr) cm−1: 3448, 3118, 2931, 1677, 1606, 1529, 1466, 1432, 1267, 1063, 774; 1H NMR (CDCl3): 61.67 (m, 2H), 1.86 (m, 2H), 2.26 (s, 3H), 2.38 (t, 2H, J=6.0 Hz), 2.72 (t, 2H, J=7.4 Hz), 6.58 (m, 1H), 7.12 (d, 1H, J=3.4 Hz), 7.63 (s, 1H), 10.7 (s, 1H); yellow solid, mp: 126-127° C. (petroleum ether).

Workup

  1. washwashed with 5% aqueous HCl (5 mL)
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue precipitated with ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-0007b7cc428c450c9f190d7ab21a0b21
Source dataset
uspto-grants-2004_04
Patent number
US06727258B2

Reaction notes

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