Chloroacetyl chloride → HCID 22839463, compound

HRID 35364Notes

Reaction equation

HRID 35364 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][NH:5][C@@H:4]2[CH2:8][CH2:9][O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C@@H:3]12.C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27]>C(Cl)Cl>[Cl:24][CH2:25][C:26]([N:5]1[CH2:6][CH2:7][O:2][C@@H:3]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][CH2:9][CH2:8][C@@H:4]12)=[O:27]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 13609761HCID 13609761, compound

Product 1

HCID 22839463HCID 22839463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.21 g of trans-3,4,4a,5,6,11b-hexahydro-2H-[1]benzoxepino[5,4-b]-1,4-oxazine hydrochloride, prepared according to the procedure of Example 2, and 1.65 ml of triethylamine in 25 ml of methylene chloride is treated dropwise with a solution of 0.70 ml of chloroacetyl chloride dissolved in 10 ml of methylene chloride. The reaction mixture is stirred overnight at room temperature, washed with a dilute solution of hydrochloric acid, followed by a water wash, a wash of dilute sodium hydroxide solution and finally by a wash of a saturated solution of sodium chloride. The reaction mixture is dried over anhydrous magnesium sulfate and evaporated to dryness to obtain 1.44 g of trans-N-chloroacetyl-3,4,4a,5,6,11b-hexahydro-2H-[1]-benzoxepino[5,4-b]-1,4-oxazine.

Workup

  1. washwashed with a dilute solution of hydrochloric acid
  2. washwash
  3. washa wash of dilute sodium hydroxide solution
  4. washfinally by a wash of a saturated solution of sodium chloride
  5. dry with materialThe reaction mixture is dried over anhydrous magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-3c8572f9eb4c498cba0e77d5e3eba59e
Source dataset
uspto-grants-1988_08
Patent number
US04766212

Reaction notes

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