4-Methylmorpholine → HCID 22672861, compound

HRID 1359162Notes

Reaction equation

HRID 1359162 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=2[CH3:26])=[CH:11][C:10]=1[S:27](Cl)(=[O:29])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.[CH2:38]([NH2:43])[C:39]([CH3:42])([CH3:41])[CH3:40]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=2[CH3:26])=[CH:11][C:10]=1[S:27]([NH:43][CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])(=[O:29])=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 79882NeopentylamineHCID 22672848HCID 22672848, compound

Product 1

HCID 22672861HCID 22672861, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the title E compound, 2-benzyloxy-5-(2,6-dimethyl-4-nitrophenoxy)benzenesulfonyl chloride (1.12 g, 2.5 mmol) in 20 mL of CH2Cl2 is treated sequentially with N-methylmorpholine (NMM; 550 mL, 5 mmol) and neopentylamine (442 mL, 3.75 mmol) at RT. After 6 h, the mixture is partitioned between water and EtOAc, and the organic solution is washed with aqueous 1N HCl and brine, dried over anhydrous Na2SO4 and concentrated to afford 2-benzyloxy-5-(2,6-dimethyl-4-nitrophenoxy)-N-(2,2-dimethylpropyl)benzenesulfonamide: NMR (CDCl3) 0.78 (s, 9H), 2.22 (s, 6H), 2.58 (d, 2H, J=7.5), 4.82 (t, 1H, J=7.5), 5.18 (s, 2H), 6.88 (dd, 1H, J=9, 3.7), 7.03, (d, 1H, J=9), 7.33-7.51 (m, 6H), 8.04 (s, 2H).

Workup

  1. customthe mixture is partitioned between water and EtOAc
  2. washthe organic solution is washed with aqueous 1N HCl and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3479dde3d0eb4f26ab0b44d38e84d38a
Source dataset
uspto-grants-2003_07
Patent number
US06599942B1

Reaction notes

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