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 1927514Notes

Reaction equation

HRID 1927514 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:27]=[C:26]([Cl:28])[C:10]2[O:11][C:12]3[C:21]([CH3:22])=[CH:20][C:19]([C:23]([OH:25])=[O:24])=[CH:18][C:13]=3[S:14](=[O:17])(=[O:16])[CH2:15][C:9]=2[CH:8]=1.N1C=CC=C[CH:30]=1>C(Cl)Cl>[CH3:30][O:24][C:23]([C:19]1[CH:20]=[C:21]([CH3:22])[C:12]2[O:11][C:10]3[C:26]([Cl:28])=[CH:27][C:7]([NH:6][C:3](=[O:4])[CH2:2][Cl:1])=[CH:8][C:9]=3[CH2:15][S:14](=[O:16])(=[O:17])[C:13]=2[CH:18]=1)=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 116317172-Amino-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda *6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid

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

Chloro-acetyl chloride (3.3 mL, 40.8 mmol) was added with stirring to a solution of the ester of Example 35j (5 g, 13.6 mmol) in CH2Cl2 (100 mL) at 15° C., followed by addition of pyridine (6.6 mL, 81.6 mmol). The reaction mixture was stirred for 2 h, concentrated, treated with water and the solid that precipitated was filtered and purified by refluxing it with stirring in ethyl acetate for 0.5 h. The solid was filtered and dried to obtain the title compound. Yield: 5.5 g, (90.9%); 1H NMR (DMSO-d6): δ 2.7 (s, 3H, CH3), 3.9 (s, 3H, OCH3), 4.31 (s, 2H, CH2), 5.4 (s, 2H, CH2), 7.71 (s, 1H, Ar), 7.9 8 (s, 1H, Ar), 8.12 (s, 1H, Ar), 8.2 (s, 1H, Ar), 10.77 (s, 1H, Ar); MS: m/e (ES−) 442 (M−1).

Workup

  1. concentrationconcentrated
  2. additiontreated with water
  3. customthe solid that precipitated
  4. filtrationwas filtered
  5. custompurified
  6. temperatureby refluxing it
  7. stirringwith stirring in ethyl acetate for 0.5 h
  8. filtrationThe solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-85b33649589642dba4309c76069f3f3d
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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