Ammonia → HCID 70465729, compound

Reaction equation

C(OC(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([S:17]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])(=[O:19])=[O:18])=[CH:9][CH:8]=1)=O)C.N.C(NS(C1C2C(=CC=CC=2)C(O)=CC=1)(=O)=[O:56])CCCCCCCCCCCCCCC>ClCCl>[CH2:21]([NH:20][S:17]([C:10]1([OH:56])[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:8][CH2:9]1)(=[O:19])=[O:18])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

Procedure

4-Ethoxycarbonyloxy-N-hexadecylnaphthalene-1-sulphonamide (21.5 g, 41.4 mmole) was added to liquid ammonia (250 ml), in portions with stirring, at -78° C. (acetone-drycold bath). The mixture was stirred for 1 h, and the excess ammonia allowed to evaporate. The residue was dissolved in ethyl acetate, washed with water and dried (MgSO4). Removal of the solvent gave a pale brown oil which was dissolved in hot dichloromethane (100ml) and then cooled in an ice-bath. The off-white precipitate was collected and dried in air to yield pure N-hexadecyl-4-hydroxynaphthalene-4-sulphonamide, 7.7 g, 42%. TLC analysis (1:3 EtOAc : 40°-60° petrol) showed one spot (Rf =0.4) and spectroscopic data was consistent with the product.