Pyridine → HCID 20162855, compound

HRID 246860Notes

Reaction equation

HRID 246860 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:12][C:13]1([S:25][CH3:26])[CH2:16][N:15]([Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C:14]1=[O:24].C(N(CC)CC)C.N1C=CC=CC=1.[O:40]([CH2:47][C:48](Cl)=[O:49])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>ClCCl>[Si:17]([N:15]1[CH2:16][C:13]([S:25][CH3:26])([NH:12][C:48](=[O:49])[CH2:47][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:14]1=[O:24])([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 69703Phenoxyacetyl chlorideHCID 14356378HCID 14356378, compound

Product 1

HCID 20162855HCID 20162855, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of (23) (830)mg) in dry dichloromethane (20 ml) at -10° C. was treated with triethylamine (220 mg) and pyridine (172 mg), followed by a solution of phenoxyacetyl chloride (372 mg) in dry dichloromethane (~4 ml). The mixture was washed with very dilute HCl, followed by brine. The organic phase was dried and the solvent evaporated. Chromatography on silica yet gave the product (24) (730 mg). νmax (CHCl3) 3400, 1745, and 1690 cm-1 ; δppm (CDCl3) (90 MHz) 0.25 and 0.27 (both s, together 6H), 0.98 (S, 9H), 2.22 (S, 3H), 3.36 and 3.81 (ABq, 2H, J7.0 Hz); 4.50 (S, 2H), 6.80 to 7.50 (m, 6H).

Workup

  1. washThe mixture was washed with very dilute HCl
  2. customThe organic phase was dried
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-77e040ec11314140a8e4b1ab62ab1448
Source dataset
uspto-grants-1987_11
Patent number
US04704385

Reaction notes

Loading…