Chloroacetyl chloride → HCID 131728447, compound

HRID 2425100Notes

Reaction equation

HRID 2425100 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-f9a051217bc74527a2d64cdc4440d217
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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