2-Methoxybenzenesulfonyl Chloride → 4-(4-Bromobenzyl)-5-((2-methoxyphenyl)sulfonyl)-3,4,5,6-tetrahydro-1H-benzo-[f][1,4]oxazocine

HRID 1429367Notes

Reaction equation

HRID 1429367 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH:7]2[NH:14][CH2:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[CH2:10][O:9][CH2:8]2)=[CH:4][CH:3]=1.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29](Cl)(=[O:31])=[O:30]>C(#N)C.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][CH:7]2[N:14]([S:29]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[O:22][CH3:21])(=[O:31])=[O:30])[CH2:13][C:12]3[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=3[CH2:10][O:9][CH2:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 37458512-Methoxybenzenesulfonyl ChlorideHCID 674173634(4-Bromobenzyl)-3,4,5,6-tetrahydro-1H-benzo[f][1,4]oxazocine

Product 1

HCID 674165884-(4-Bromobenzyl)-5-((2-methoxyphenyl)sulfonyl)-3,4,5,6-tetrahydro-1H-benzo-[f][1,4]oxazocineYield 38%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

To a mixture of compound 3l (900 mg, 2.7 mmol) and TEA (546 mg, 5.4 mmol) in acetonitrile (30 mL) was added 2-methoxybenzene sulfonyl chloride (559 mg, 2.7 mmol) and catalytic amount of DMAP. The reaction mixture was stirred at rt overnight. The solvent was evaporated in vacuo and purified by CC to give 3 as a white solid (510 mg, 38% yield).

Workup

  1. customThe solvent was evaporated in vacuo
  2. custompurified by CC

Sources & evidence

ORD record
ord-b1e313ab658c485890c85a8ff3cdb601
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

Loading…