m-Chloroperbenzoic acid → HCID 10625730, compound

HRID 2081657Notes

Reaction equation

HRID 2081657 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[C:16]=1[NH:24][C:25]([NH:27][C:28]1[NH:32][C:31]([S:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[N:30][N:29]=1)=[O:26])[CH3:14]>ClCCl>[CH3:14][CH:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:22])[CH3:23])[C:16]=1[NH:24][C:25]([NH:27][C:28]1[N:32]=[C:31]([S:33]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[O:9])[NH:30][N:29]=1)=[O:26])[CH3:12]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 178443213HCID 178443213, compound

Product 1

HCID 10625730HCID 10625730, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperbenzoic acid (0.26 g, 1.49 mmol) was added to a cooled (0° C.) solution of the compound of Example 15 in dichloromethane (25 mL). The solution was allowed to warm to room temperature and stirred for 4 hours. The mixture was diluted with CH2Cl2 (100 mL) and washed sequentially with NaHSO3, water, NaHCO3, and brine, dried over Na2SO4, concentrated, and triturated with hexane to give a white solid which was filtered and dried in vacuo to yield 0.42 g; m.p. 178°-181° C.

Workup

  1. washwashed sequentially with NaHSO3, water, NaHCO3, and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customtriturated with hexane
  5. customto give a white solid which
  6. filtrationwas filtered
  7. customdried in vacuo
  8. customto yield 0.42 g

Sources & evidence

ORD record
ord-8011b0e7504c4b0bb1e74a0bfba0d26f
Source dataset
uspto-grants-1993_02
Patent number
US05185358

Reaction notes

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