Hydrochloric Acid → HCID 136347868, compound

HRID 1786169Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]2[NH:10][N:11]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:13]=2)[CH:3]=1.Cl[CH2:18][C:19](Cl)=[O:20].[OH-].[Na+].Cl>O1CCOCC1.N1C=CC=CC=1.C(OCC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:19](=[O:20])[CH2:18][N:10]3[C:9](=[N:13][C:12]([CH:14]4[CH2:16][CH2:15]4)=[N:11]3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A suspension of 4-chloro-2-(5-cyclopropyl-2H-[1,2,4]triazol-3-yl)-phenylamine (3.95 g, 16.8 mmol) in dioxane (120 mL) and pyridine (1.5 mL) was cooled to 10° C. A solution of chloroacetyl chloride (1.54 mL, 19.3 mmol) in diethylether (5 mL) was then added dropwise over 15 min. The reaction mixture was stirred at this temperature for 30 min and was then treated within 10 min with aqueous sodium hydroxide (2 N, 20.2 mL, 40.4 mmol). The mixture was stirred for 22 h at ambient temperature. After the addition of aqueous HCl (1 N, 2.5 mL) the resulting mixture was evaporated. The residue was stirred for 45 min in water (100 mL) and ethyl acetate (5 mL). The resulting crystals were filtered off and washed with water. Drying in vacuo and trituration with ethyl acetate afforded the title compound (3.02 g, 65%) which was obtained as an off-white solid. MS: m/e=275.0 [M+H]+.

Workup

stirringThe mixture was stirred for 22 h at ambient temperature
customwas evaporated
stirringThe residue was stirred for 45 min in water (100 mL)
filtrationThe resulting crystals were filtered off
washwashed with water
dry with materialDrying in vacuo and trituration with ethyl acetate

Sources & evidence

ORD record: ord-3fb94c1777df47b18fb32b5778c33b28
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507729B2

Reaction notes

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