Phosgene → 7-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl chloride

HRID 2224068Notes

Reaction equation

HRID 2224068 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[C:5]1([S:11]([C:14]2[CH:23]=[CH:22][C:17]3[NH:18][CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C>ClCCl>[C:5]1([S:11]([C:14]2[CH:23]=[CH:22][C:17]3[N:18]([C:1]([Cl:4])=[O:2])[CH2:19][CH2:20][O:21][C:16]=3[CH:15]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 586415137-benzenesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine

Product 1

HCID 586415087-Benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phosgene (1.44 mL of a 1.8 M solution in dichloromethane, 2.64 mmol) at 0° C. was added a solution of 7-benzenesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine (0.663 g., 2.4 mmol) in 3 mL dichloromethane followed by dropwise addition of triethylamine (0.361 mL, 2.6 mmol) over three minutes. The reaction was allowed to warm to room temperature and was stirred for an hour. The reaction mixture was then concentrated in vacuo, and then dissolved in 50 mL dichloromethane which was removed in vacuo. A suspension of the crude residue in 60 mL of 1:1 ethyl ether: hexanes was washed with 3 times with 50 mL of 6N aqueous hydrogen chloride. The organic fractions were dried over MgSO4 and concentrated in vacuo to give 7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl chloride, which was used directly in the following step.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutiondissolved in 50 mL dichloromethane which
  3. customwas removed in vacuo
  4. additionA suspension of the crude residue in 60 mL of 1:1 ethyl ether
  5. washhexanes was washed with 3 times with 50 mL of 6N aqueous hydrogen chloride
  6. dry with materialThe organic fractions were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82ca1805fe8f4abbac422543db565948
Source dataset
uspto-grants-2008_05
Patent number
US07378415B2

Reaction notes

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