Hydrochloric Acid → HCID 86745789, compound

HRID 1196227Notes

Reaction equation

HRID 1196227 reaction equation
Cl[CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[C:5]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[SH:29][CH2:30][C:31]([OH:33])=[O:32].C(N(CC)CC)C.Cl>CN(C)C=O>[C:31]([CH2:30][S:29][CH2:2][C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[C:5]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([OH:33])=[O:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 8471TriethylamineHCID 86745790HCID 86745790, compound

Product 1

HCID 86745789HCID 86745789, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To 5.96 g of 6-(chloromethyl)-4,5-bis(phenylmethoxy)-2-pyridinecarboxylic acid, methyl ester 0.25 g KI dissolved in 30 ml dimethylformamide, was added a solution of 1.38 g mercaptoacetic acid and 3.04 g triethylamine in 30 ml dimethylformamide. After stirring overnight the formed triethylamne/HCl was filtered off, and the dimethylformamide of the filtrate distilled off in vacuo . The residue was stirred with water/ethylacetate and the pH was adjusted to 2 with 2n HCl. The organic phase was washed with water, dried and evaporated, 6.8 g solid of title compound. Crystallization from ethanol yielded 3.01 g title compound and from the concentrated filtrate another batch of 0.37 g title compound was obtained. M.P. 135° C.

Workup

  1. filtrationwas filtered off
  2. distillationthe dimethylformamide of the filtrate distilled off in vacuo
  3. washThe organic phase was washed with water
  4. customdried
  5. customevaporated
  6. customCrystallization from ethanol

Sources & evidence

ORD record
ord-236e10f17ff848fdb1a97bd69e1003b3
Source dataset
uspto-grants-1992_05
Patent number
US05112968

Reaction notes

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