Acetyl chloride → HCID 13092036, compound

HRID 1163946Notes

Reaction equation

HRID 1163946 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([CH:8]2[O:12][C:11](=[O:13])[NH:10][C:9]2=[O:14])[CH:7]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:26])[CH3:25]>ClCCCl>[C:24]([N:10]1[C:9](=[O:14])[CH:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:15][CH3:16])[O:12][C:11]1=[O:13])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 13092002HCID 13092002, compound

Product 1

HCID 13092036HCID 13092036, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

At room temperature, 5-(5-chloro-2-methoxyphenyl)-oxazolidine-2,4-dione (1.21 g., 5 mmoles) was suspended in 25 ml. of 1,2-dichloroethane. Triethylamine (505 mg., 0.7 ml., 5 mmoles) was added and the mixture stirred for 1 minutes to achieve solution. Acetyl chloride (393 mg., 0.36 ml., 5 mmoles) was added and the mixture stirred for 1 hour. The reaction mixture was concentrated to 5 ml., and solids precipitated by the addition of about 25 ml. of ether. The isolated solids were distributed between chloroform and saturated sodium bicarbonate. The organic phase was separated, washed with fresh bicarbonate and then with brine, dried over anhydrous magnesium sulfate and evaporated to yield 3-acetyl-5-(5-chloro-2-methoxyphenyl)oxazolidine-2,4-dione [910 mg., 64%; m.p. 161°-164° C.; pnmr/DMSO-d6 /delta 2.5 (s, 3H), 3.9 (s, 3H), 6.0 (s, 1H, 7.4 (m, 3H)].

Workup

  1. customAt room temperature
  2. stirringthe mixture stirred for 1 hour
  3. concentrationThe reaction mixture was concentrated to 5 ml
  4. custom, and solids precipitated by the addition of about 25 ml
  5. customThe organic phase was separated
  6. washwashed with fresh bicarbonate
  7. dry with materialwith brine, dried over anhydrous magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-589c10b5388d412b850aba6244ea5ea3
Source dataset
uspto-grants-1983_01
Patent number
US04367234

Reaction notes

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