Pyridine → 4-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1695264Notes

Reaction equation

HRID 1695264 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:29])[C:13]2[O:19][C:18]3[C:20]([Cl:25])=[CH:21][C:22]([NH2:24])=[CH:23][C:17]=3[CH2:16][S:15](=[O:27])(=[O:26])[C:14]=2[CH:28]=1)=[O:9].N1C=CC=CC=1>ClCCl>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:29])[C:13]2[O:19][C:18]3[C:20]([Cl:25])=[CH:21][C:22]([NH:24][C:3](=[O:4])[CH2:2][Cl:1])=[CH:23][C:17]=3[CH2:16][S:15](=[O:27])(=[O:26])[C:14]=2[CH:28]=1)=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 115596902-Amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda *6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 116336414-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetylchloride (3.3 mL, 40.8 mmol) was added to the solution of compound of Example 1 (5 g, 13.6 mmol) in dichloromethane (100 mL) at 20° C. Pyridine (6.6 mL, 81.6 mmol) was added and the reaction mixture was stirred for 2 h. The solvent was removed under vacuum and water (200 mL) was added. The solid obtained was filtered, washed with water and purified by stirring in ethyl acetate (200 mL) at reflux condition for 30 min. The solid was filtered and dried to obtain the title compound. Yield: 4.86 g (80.1%); mp 292-293° C.; 1H NMR (DMSO-d6, 300 MHz): δ 2.64 (s, 3H, CH3), 3.86 (s, 3H, OCH3), 4.27 (s, 2H, CH2), 5.34 (s, 2H, CH2), 7.67 (s, 1H, Ar), 7.88 (s, 1H, Ar), 8.11 (s, 1H, Ar), 8.15 (s, 1H, Ar), 10.70 (s, 1H, NH); MS: m/e (ES+) 445 (M+1); analysis: C18H15Cl2NO6S requires C, 48.66,H, 3.40, N, 3.15, Cl, 15.96, S, 7.22; found: C, 48.09,H, 3.37, N, 3.38, Cl, 16.37, S, 7.72%.

Workup

  1. customThe solvent was removed under vacuum and water (200 mL)
  2. additionwas added
  3. customThe solid obtained
  4. filtrationwas filtered
  5. washwashed with water
  6. custompurified
  7. stirringby stirring in ethyl acetate (200 mL)
  8. temperatureat reflux condition for 30 min
  9. filtrationThe solid was filtered
  10. customdried

Sources & evidence

ORD record
ord-4d1a63dde439437db62323bf687d9bbe
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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