Benzene → HCID 131728530, compound

HRID 2425103Notes

Reaction equation

HRID 2425103 reaction equation
[Na].[BH4-].[Cl:3][CH2:4][C:5](O)=O.C1C=CC=CC=1.[CH3:14][O:15][C:16]([C:18]1[CH:19]=[C:20]([CH3:41])[C:21]2[O:27][C:26]3[C:28]([Cl:37])=[CH:29][C:30]([NH:32][CH2:33][CH2:34][CH2:35][Cl:36])=[CH:31][C:25]=3[CH2:24][S:23](=[O:39])(=[O:38])[C:22]=2[CH:40]=1)=[O:17]>C1COCC1>[CH3:14][O:15][C:16]([C:18]1[CH:19]=[C:20]([CH3:41])[C:21]2[O:27][C:26]3[C:28]([Cl:37])=[CH:29][C:30]([N:32]([CH2:5][CH2:4][Cl:3])[CH2:33][CH2:34][CH2:35][Cl:36])=[CH:31][C:25]=3[CH2:24][S:23](=[O:38])(=[O:39])[C:22]=2[CH:40]=1)=[O:17]

Participants

6

Reactant 4

HCID 241BenzeneHCID 300Chloroacetic AcidHCID 131720715CID 131720715HCID 1317285294-Chloro-2-(3-chloropropylamino)-6-methyl-10,10dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 131728530HCID 131728530, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Powdered sodium-borohydride (0.33 g, 8.6 mmol) was added in portions at 0° C., to a solution of chloroacetic acid (1.68 g, 17 mmol) in THF (6 mL), and benzene (90 mL). Reaction mixture was warmed to room temperature and stirred for 1 h, and compound of Example 29a (1.3 g, 2.9 mmol) was added. Reaction mixture was refluxed for 3 h. Reaction mixture was cooled and quenched using sodium bicarbonate solution, and extracted with ethylacetate. Organic layer was washed with water (100 mL) and brine (50 mL). The crude product obtained was purified by column chromatography (silica gel, ethylacetate/pet-ether) to obtain the title compound. Yield: 1.25 g (87%); 1H NMR (DMSO-d6, 300 MHz): δ 2.00 (t, 2H, CH2), 2.63 (s, 3H, CH3), 3.66 (t, 2H, CH2), 3.69-3.80 (m, 6H, 3×CH2), 3.85 (s, 3H, OCH3), 5.16 (s, 2H, CH2), 6.74 (s, 1H, Ar), 6.85 (s, 1H, Ar), 8.08 (s, 1H, Ar), 8.14 (s, 1H, Ar); MS: m/e (EI) 506 (M+).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. temperaturewas refluxed for 3 h
  4. customReaction mixture
  5. temperaturewas cooled
  6. customquenched
  7. extractionextracted with ethylacetate
  8. washOrganic layer was washed with water (100 mL) and brine (50 mL)
  9. customThe crude product obtained
  10. customwas purified by column chromatography (silica gel, ethylacetate/pet-ether)

Sources & evidence

ORD record
ord-db29b3a573b64a52a64f740070f84885
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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