Triethylamine → HCID 11246633, compound

HRID 1296518Notes

Reaction equation

HRID 1296518 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][C:9](=[O:11])[O:8][C:7]([CH3:13])([CH3:12])[C:6]=2[CH:14]=1.C(N(CC)CC)C.[Cl:22][C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH3:13][C:7]1([CH3:12])[C:6]2[CH:14]=[C:2]([O:1][S:30]([C:24]3[CH:25]=[CH:26][CH:27]=[C:28]([Cl:29])[C:23]=3[Cl:22])(=[O:32])=[O:31])[CH:3]=[CH:4][C:5]=2[NH:10][C:9](=[O:11])[O:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27342222,3-Dichlorobenzene-1-sulfonyl chlorideHCID 132604826-hydroxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

Product 1

HCID 11246633HCID 11246633, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-hydroxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (1.00 g, 5.17 mmol), prepared according to the procedure in example 69, in methylene chloride (25 mL) at 0° C. was added triethylamine (0.9 mL, 6.45 mmol). After 10 minutes, 2,3-dichlorobenzenesulfonyl chloride (1.27 g, 5.17 mmol) was added. The solution was stirred for one hour, then partitioned between ammonium chloride solution (sat.) and methylene chloride. The organic layer was dried over magnesium sulfate and concentrated. Trituration with ether gave (4,4-dimethyl-2-oxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl)-2,3-dichlorobenzenesulfonate as a white solid (1.55 g, 75%). 1H NMR (DMSO-d6): δ 10.37 (s, 1H), 8.13 (dd, J=8.2, 1.6 Hz, 1H), 7.90 (dd, J=7.9, 1.5 Hz, 1H), 7.60 (t, J=8.05 Hz, 1H), 7.02 (dd, J=8.7, 2.6 Hz, 1H), 6.96 (d, J=2.7 Hz, 1H), 6.87 (d, J=8.7 Hz, 1H), 1.48 (s, 6H). MS (ESI) m/z 400/402/404 ([M−H]−); Anal. calcd for C16H13Cl2NO5S: C, 47.78; H, 3.26 N, 3.48. Found: C, 47.14; H, 3.46; N, 3.49.

Workup

  1. custompartitioned between ammonium chloride solution (sat.) and methylene chloride
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-155499b9cbc24fc2a242b13235907b9a
Source dataset
uspto-grants-2007_07
Patent number
US07247625B2

Reaction notes

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