Benzoyl chloride → HCID 22411748, compound

HRID 1728773Notes

Reaction equation

HRID 1728773 reaction equation
Cl.[NH2:2][CH:3]([C:14](=[O:31])[CH2:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[C:19]([C:27]([F:30])([F:29])[F:28])[CH:18]=1)[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>N1C=CC=CC=1>[C:32]([NH:2][CH:3]([C:14](=[O:31])[CH2:15][CH2:16][C:17]1[CH:22]=[C:21]([C:23]([F:25])([F:24])[F:26])[CH:20]=[C:19]([C:27]([F:28])([F:29])[F:30])[CH:18]=1)[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 22905844HCID 22905844, compound

Product 1

HCID 22411748HCID 22411748, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound of Example 11 (0.55 g) was dissolved in pyridine (10 ml) and benzoyl chloride (0.17 g) was added. The reaction was stirred for 16 hours and then partitioned between 10% citric acid (50 ml) and ethyl acetate (100 ml). The organic phase was washed with water (100 ml) and sodium bicarbonate solution (100 ml), dried (MgSO4) and evaporated to yield an oil which was purified by chromatography on silica using petroleum ether/ethyl acetate (1:3) to yield the title compound as a white solid, mp=119°-122° C.; found: C, 63.28; H, 4.25; N, 5.14; C28H22F6N2O2 requires C, 63.16, H, 4.16; N, 5.26%.

Workup

  1. custompartitioned between 10% citric acid (50 ml) and ethyl acetate (100 ml)
  2. washThe organic phase was washed with water (100 ml) and sodium bicarbonate solution (100 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto yield an oil which
  6. customwas purified by chromatography on silica

Sources & evidence

ORD record
ord-730f55c0abe8451dbe1cadb31865108d
Source dataset
uspto-grants-1994_07
Patent number
US05328927

Reaction notes

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