Chloroacetyl chloride → HCID 54541875, compound

HRID 35360Notes

Reaction equation

HRID 35360 reaction equation
Cl.[CH2:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]2[C@@H:11]3[C@@H:16]([CH2:17][CH2:18][O:19][C:7]=2[CH:6]=1)[NH:15][CH2:14][CH2:13][O:12]3)[CH3:3].C(N(CC)CC)C.[Cl:27][CH2:28][C:29](Cl)=[O:30]>C(Cl)Cl>[Cl:27][CH2:28][C:29]([N:15]1[CH2:14][CH2:13][O:12][C@@H:11]2[C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:2][CH3:3])=[CH:6][C:7]=3[O:19][CH2:18][CH2:17][C@@H:16]12)=[O:30]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 70404687HCID 70404687, compound

Product 1

HCID 54541875HCID 54541875, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1.21 g of trans-3,4,4a,5,6,11b-hexahydro-9-ethoxy-2H-[1]benzoxepino[5,4-b]-1,4-oxazine hydrochloride, prepared via an analogous procedure to the preceding Example, 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-9-ethoxy-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-f77d9dc8d79e406e89e830f2b5e3a222
Source dataset
uspto-grants-1988_08
Patent number
US04766212

Reaction notes

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