Benzoyl chloride → HCID 13032033, compound

HRID 845248Notes

Reaction equation

HRID 845248 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH2:8].C(N(CC)CC)C.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl.C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH:8][C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamine

Product 1

HCID 13032033HCID 13032033, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.00 g (8.55 mmol) of O-tetrahydropyran-2-ylhydroxylamine (prepared as described in U.S. Pat. No. 4,607,053, Example 2, Part A) and 1.4 ml (10 mmol) of sieve-dried triethylamine in 15 ml of dry CH2Cl2 cooled to -20 was added a solution of 1.50 g (10.7 mmol) of benzoyl chloride in 5 ml of CH2Cl2 over 10 minutes. The reaction mixture was stirred for 1 hour then diluted with 15 ml of ethyl acetate. The resulting slurry was filtered and the filtrate concentrated in vacuo to give a solid. Recrystallization (EtOAc/petroleum ether) of the solid afforded 1.45 g (77%) of title compound as white crystals, m.p. 130°-134°.

Workup

  1. filtrationThe resulting slurry was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give a solid
  4. customRecrystallization (EtOAc/petroleum ether) of the solid

Sources & evidence

ORD record
ord-a7c4e1d1a15c4fe1a9f89e0c0e26d8ea
Source dataset
uspto-grants-1988_07
Patent number
US04757078

Reaction notes

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