Chloroacetyl chloride → 2-Chloro-N-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamide

HRID 1760674Notes

Reaction equation

HRID 1760674 reaction equation
C(C([C:6]1[C:7]([NH2:24])=[C:8]([NH2:23])[C:9]([O:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])=[N:10][C:11]=1[CH3:12])CC)C.[Cl:25][CH2:26][C:27](Cl)=[O:28].C(N([CH2:35][CH3:36])CC)C.[CH2:37]1[CH2:41]OC[CH2:38]1>>[Cl:25][CH2:26][C:27]([NH:23][C:8]1[C:9]([O:13][C:14]2[C:15]([CH3:22])=[CH:16][C:17]([CH3:21])=[CH:18][C:19]=2[CH3:20])=[N:10][C:11]([CH3:12])=[CH:6][C:7]=1[NH:24][CH:38]([CH2:35][CH3:36])[CH2:37][CH3:41])=[O:28]

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 867595891-Ethyl-propyl-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine

Product 1

HCID 120183492-Chloro-N-[4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridin-3-yl]-acetamide

Procedure

To a solution of N+(1-ethyl-propyl-6-methyl-2-(2,4,6-trimethyl-phenoxy)-pyridine-3,4-diamine (250 mg, 0.763 mmol) in dry THF was added chloroacetyl chloride (86 mg, 0.763 mmol) and triethylamine (77 mg, 0.763 mmol) at 0° C. The resulting mixture was warmed to room temperature and stirred for 1 hr. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to dryness to give the title compound as a solid. The solid was purified through silica gel column chromatography to give 280 mg(91%) of tan crystals, mp. 152-154° C.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9f338a7e454747798e66212fc63edc6f
Source dataset
uspto-grants-2005_01
Patent number
US06844351B1

Reaction notes

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