Acetyl chloride → HCID 67025493, compound

HRID 1992274Notes

Reaction equation

HRID 1992274 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[CH2:13][CH2:12][S:11][C:10]([NH2:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:25])[CH3:24]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:15])[CH2:13][CH2:12][S:11][C:10]([NH:14][C:23](=[O:25])[CH3:24])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57627869HCID 57627869, compound

Product 1

HCID 67025493HCID 67025493, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of 4-(3-bromo-phenyl)-4-methyl-5,6-dihydro-4H-[1,3]thiazin-2-ylamine (10 g, 35 mmoles, 1 equiv) and triethylamine (4.3 g, 42 mmoles, 1.2 equiv) in dichloromethane (70 mL) is added dropwise acetyl chloride (2.8 g, 35 mmoles, 1 equiv) over 5 minutes. The reaction is allowed to warm to ambient temperature. After 1 h, the reaction is diluted with dichloromethane and extracted with water. The organic layers are separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by silica gel chromatography eluting with hexane:ethyl acetate (1:1) to give the title compound (87% yield): MS (m/z): 327, 329 (M+1).

Workup

  1. extractionextracted with water
  2. customThe organic layers are separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel chromatography
  7. washeluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-003dfa178c984cad89a5ea3ae6f34b09
Source dataset
uspto-grants-2010_01
Patent number
US07648983B2

Reaction notes

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