Chloroacetyl chloride → HCID 18172722, compound

HRID 395227Notes

Reaction equation

[Cl:1][CH2:2][C:3](Cl)=[O:4].[OH:6][C:7]1[C:16]([NH2:17])=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[CH:10][CH:11]=[C:12]2[NH:18][S:19]([CH3:22])(=[O:21])=[O:20].C(=O)([O-])[O-].[Ca+2]>O1CCOCC1>[CH3:22][S:19]([NH:18][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH:14]=[CH:15][C:16]([NH:17][C:3](=[O:4])[CH2:2][Cl:1])=[C:7]2[OH:6])(=[O:21])=[O:20]

Participants

Conditions

Temperature: 85 °C

Procedure

0.32 ml of chloroacetyl chloride (4 mmol) was introduced into a suspension of 1 g of N-(5-hydroxy-6-aminonaphthalen-1-yl)methanesulphonamide (4 mmol, prepared according to the method described in Patent U.S. Pat. No. 4,956,456) and 0.4 g of calcium carbonate (4 mmol) in 50 ml of dioxane, with stirring and under an inert atmosphere. The reaction medium was stirred for 2 hours at 85° C. and then cooled to 30° C. The suspension was filtered on sintered glass and the inorganic salts were rinsed twice with a minimum of dioxane. The combined organic phases were poured over 100 ml of ice-cold water. The precipitate formed was drained, washed twice with water and dried under vacuum to constant weight to give 1.12 g of N-(5-methanesulphonylamino-1-hydroxynaphthalen-2-yl)-2-chloroacetamide in the form of a pink powder, with a yield of 84%.

Workup

customprepared
temperaturecooled to 30° C
filtrationThe suspension was filtered on sintered glass
washthe inorganic salts were rinsed twice with a minimum of dioxane
additionThe combined organic phases were poured over 100 ml of ice-cold water
customThe precipitate formed
washwashed twice with water
customdried under vacuum to constant weight

Sources & evidence

ORD record: ord-366d5c4a6a824d3d9e20b7ad37654f04
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605124B1

Reaction notes

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