Sodium Sulfite → HCID 19894055, compound

HRID 892746Notes

Reaction equation

HRID 892746 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[N:14]=[C:15]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]([C:28]2[CH:33]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([N+:40]([O-:42])=[O:41])[CH:35]=3)[C:32]([C:43]([O:45][CH3:46])=[O:44])=[C:31]([CH3:47])[NH:30][C:29]=2[CH3:48])=[O:27])[S:16][CH:17]=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[CH3:12][C:13]1[N:14]=[C:15]([S:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][O:25][C:26]([C:28]2[CH:33]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([N+:40]([O-:42])=[O:41])[CH:35]=3)[C:32]([C:43]([O:45][CH3:46])=[O:44])=[C:31]([CH3:47])[NH:30][C:29]=2[CH3:48])=[O:27])=[O:9])[S:16][CH:17]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 19894052HCID 19894052, compound

Product 1

HCID 19894055HCID 19894055, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (0.156g, 0.001 mol) in dichloromethane (5mL) was added to a solution of 3-[6-(4-methylthiazol-2-yl) thiohexyloxy-carbonyl]-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine (18) (0.545 g, 0.001 mol) in dichloromethane (10 mL) at room temperature with agitation. Stirring under the same conditions was maintained for 2 h. The excess peracid was decomposed by 10% solution of sodium sulfite. The organic layer was separated and washed with 5% sodium bicarbonate solution in order to extract m-chlorobenzoic acid, followed by washing with water and drying over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residual oil was purified by elution from a silica gel column using chloroform-hexane (8:2, v/v) as eluant to give 3-[6-(4-methylthiazol-2-yl)sulfinylhexyloxycarbonyl]-5-methoxycarbonyl-2,6-dimethyl-4-(3- nitrophenyl)-1,4-dihydropyridine (65%) as colorless prisms, mp 81°-83° C. IR (KBr) 3365 (NH) 1695 and 1652 (CO2R) 1033 (SO)cm-1, NMR (CDCl3) 1.22-1.74 (m, 8H, (CH2)4), 2.36 (S, 6H, Me-2, Me-6) 2.52 (S, 3H, Me-HEt),3.02-3.22 (m, 2H, CH2 --SO), 3.68 (S, 3H, CO2Me), 3.96-4.14 (m, 2H, CH2 --O), 5.12 (S, 1H, H-4), 6.56 (S, 1H, H-HEt), 7.26 (S, 1H, NH), 7.38-8.14 (m, 4H, H-2', H-4', H-5', H-6'). Analysis found: C, 55.75; H, 5.64; N, 7.35; S, 11.30. Required: C, 55.66; H, 5.56; N, 7.48; S, 11.42 (C26H31N3O7S2). ##STR7##

Workup

  1. temperaturewas maintained for 2 h
  2. customThe organic layer was separated
  3. washwashed with 5% sodium bicarbonate solution in order
  4. extractionto extract m-chlorobenzoic acid
  5. washby washing with water
  6. dry with materialdrying over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residual oil was purified by elution from a silica gel column

Sources & evidence

ORD record
ord-5b37fca042254777997a3185eff4006f
Source dataset
uspto-grants-1992_06
Patent number
US05120750

Reaction notes

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