4-Methylmorpholine → HCID 22672861, compound

HRID 2120301Notes

Reaction equation

HRID 2120301 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-4e19c0104b32453e87af85afc42e2d9d
Source dataset
uspto-grants-2004_02
Patent number
US06689896B2

Reaction notes

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