m-Chloroperbenzoic acid → HCID 54410203, compound

HRID 1649273Notes

Reaction equation

HRID 1649273 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]([O:25][C:26]([C:28]1[N:29]2[CH:32]([S:33][CH2:34][C:35]=1[CH2:36][CH:37]([Cl:39])[Cl:38])[CH:31]([NH:40][C:41](=[O:71])[C:42](=[N:68][O:69][CH3:70])[C:43]1[N:44]=[C:45]([NH:48][C:49]([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[S:46][CH:47]=1)[C:30]2=[O:72])=[O:27])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl.C(OCC)(=O)C>[CH:12]([O:25][C:26]([C:28]1[N:29]2[CH:32]([S:33](=[O:9])[CH2:34][C:35]=1[CH2:36][CH:37]([Cl:39])[Cl:38])[CH:31]([NH:40][C:41](=[O:71])[C:42](=[N:68][O:69][CH3:70])[C:43]1[N:44]=[C:45]([NH:48][C:49]([C:56]3[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=3)([C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)[C:50]3[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=3)[S:46][CH:47]=1)[C:30]2=[O:72])=[O:27])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 54407251HCID 54407251, compound

Product 1

HCID 54410203HCID 54410203, compoundYield 73.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 85% pure meta-chloroperbenzoic acid (0.05 g) in methylene chloride (1 cc) is added all at once to a solution, cooled to -10° C., of product (13d) (0.2 g) in methylene chloride (5 cc). After 30 minutes at -10° C., the reaction mixture is diluted with ethyl acetate (20 cc) and washed with a saturated solution of sodium bicarbonate (2×10 cc) and a saturated solution of sodium chloride (2×10 cc). After the organic phase has been dried over sodium sulphate and concentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C., a crude product (13a) (0.15 g) is obtained in the form of a hard orange foam.

Workup

  1. washwashed with a saturated solution of sodium bicarbonate (2×10 cc)
  2. dry with materialAfter the organic phase has been dried over sodium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (30 mm Hg; 4 kPa) at 30° C.

Sources & evidence

ORD record
ord-e9b1dd7d2e494f2480c2395d4e0781c3
Source dataset
uspto-grants-1983_11
Patent number
US04415562

Reaction notes

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