Chloroacetyl chloride → HCID 131728447, compound

HRID 1695286Notes

Reaction equation

HRID 1695286 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:27])[C:8]2[O:14][C:13]3[C:15]([Cl:23])=[CH:16][C:17]([NH:19][CH2:20][CH2:21][Cl:22])=[CH:18][C:12]=3[CH2:11][S:10](=[O:25])(=[O:24])[C:9]=2[CH:26]=1)=[O:4].[Cl:28][CH2:29][C:30](Cl)=[O:31]>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH3:27])[C:8]2[O:14][C:13]3[C:15]([Cl:23])=[CH:16][C:17]([N:19]([C:30](=[O:31])[CH2:29][Cl:28])[CH2:20][CH2:21][Cl:22])=[CH:18][C:12]=3[CH2:11][S:10](=[O:24])(=[O:25])[C:9]=2[CH:26]=1)=[O:4]

Participants

3

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 1317284464-Chloro-2-(2-chloro-ethylamino)-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 131728447HCID 131728447, compound

Conditions

Temperature
90 °C

Procedure

4-Chloro-2-(2-chloro-ethylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid methyl ester (prepared by following the method described in example 29a or example 29b, 1.9 gm, 4.4 mmol) was added to chloroacetyl chloride (6 mL) at room temperature. Reaction mixture was then stirred at 90° C. for 1 h. Reaction mixture was cooled and diluted using ice water (100 mL). The solid separated was filtered, washed with water and dried to obtain the title compound. Yield: 1.85 g, (83%); 1H NMR (DMSO-d6, 300 MHz): δ 2.60 (s, 3H, CH3), 3.67 (t, 2H, CH2), 3.88 (s, 3H, OCH3), 3.99 (t, 2H, CH2), 4.27 (bs, 2H,CH2), 5.31 (s, 2H, CH2), 7.66 (s, 1H, Ar), 7.80 (s, 1H, Ar), 8.17 (s, 1H, Ar), 8.19 (s, 1H, Ar); MS: m/e (ES+) 505 (M+1).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. temperaturewas cooled
  4. additiondiluted
  5. customThe solid separated
  6. filtrationwas filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-981c0feb21b94ed1bff5e51ce0a0078e
Source dataset
uspto-grants-2012_04
Patent number
US08163730B2

Reaction notes

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