Acetyl chloride → HCID 66856036, compound

HRID 1034599Notes

Reaction equation

HRID 1034599 reaction equation
[CH2:1]([C:8]1[C:31](=[O:32])[N:11]2[CH:12]=[C:13]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[NH:14][C:15]([S:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[C:10]2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33](Cl)(=[O:35])[CH3:34]>ClCCl.CN(C)C1C=CN=CC=1>[C:33]([O:32][C:31]1[N:11]2[CH:12]=[C:13]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:14]=[C:15]([S:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C:10]2=[N:9][C:8]=1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:35])[CH3:34]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 178492789HCID 178492789, compound

Product 1

HCID 66856036HCID 66856036, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 231 (25 mg, 0.06 mmol) in 4 mL of dichloromethane, acetyl chloride (8 μL, 0.12 mmol) and 4-(dimethylamino)pyridine (DMAP) (5 mg, 0.03 mmol) were added, the resulting mixture was stirred at room temperature for 15 min. Then the solution was washed with water and the organic layer was dried over Na2SO4, filtered and the solvent removed under reduced pressure to obtain 18 mg (yield 66%) of 25a as a red oil. 1H-NMR (CDCl3): 2.10 (s, 3H), 3.88 (s, 3H), 4.20 (s, 2H), 7.00-7.02 (m, 2H), 7.22-7.33 (m, 8H), 7.61-7.64 (m, 4H), 7.68 (s, 1H). MS (ESI): m/z 482 (M+H+).

Workup

  1. washThen the solution was washed with water
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c64fe8931435479e8b0e4572e241bf33
Source dataset
uspto-grants-2013_10
Patent number
US08546147B2

Reaction notes

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