Triethylamine → HCID 9867359, compound

HRID 846644Notes

Reaction equation

HRID 846644 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:13][CH3:14])[CH:7]=[CH:8][CH:9]=2)[O:4]1.Br[CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[S:21]1(=[O:23])=[O:22].C(N(CC)CC)C>CN(C)C=O>[O:22]=[S:21]1(=[O:23])[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:29]=2[C:30](=[O:31])[N:20]1[CH2:19][CH2:18][CH2:17][CH2:16][NH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:13][CH3:14])[CH:7]=[CH:8][CH:9]=2)[O:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107817741,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-oneHCID 15057554HCID 15057554, compound

Product 1

HCID 9867359HCID 9867359, compoundYield 21.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.3 g (0.027 mol) 2-aminomethyl-8-methoxychroman from example 93g, 9.5 g (0.03 mol) N-(4-bromobutyl)saccharin, 3.05 g (0.03 mol) triethylamine and 80 ml dimethylformamide were heated to 50° C. for 4h. Work-up as described in example 93h furnished 16.6 g crude product, which was filtered through 175 g silica with toluene/ethyl acetate. This gave 3.4 g dialkylation product and 7.1 g monoalkylation product. Rechromatography of the monoalkylation product on 230 g silica with toluene/methanol (10:1) gave 2.5 g pure 2-{N-[4-(1,1-dioxido-3-oxo-2,3-dihydro-benzisothiazol-2-yl)butyl]aminomethyl}-8-methoxy-chroman.

Workup

  1. customfurnished 16.6 g crude product, which
  2. filtrationwas filtered through 175 g silica with toluene/ethyl acetate

Sources & evidence

ORD record
ord-b0e32834058f4b229e2de577dbdc1115
Source dataset
uspto-grants-1992_08
Patent number
US05137901

Reaction notes

Loading…