Ammonia → HCID 70465729, compound

HRID 1979606Notes

Reaction equation

HRID 1979606 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

5

Reactant 3

HCID 222AmmoniaHCID 20439471HCID 20439471, compoundHCID 20439498HCID 20439498, compound

Product 1

HCID 70465729HCID 70465729, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. customto evaporate
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent
  6. customgave a pale brown oil which
  7. temperaturecooled in an ice-bath
  8. customThe off-white precipitate was collected
  9. customdried in air

Sources & evidence

ORD record
ord-ac3b09cc45e146dabf80f4d68885e1d5
Source dataset
uspto-grants-1984_11
Patent number
US04481268

Reaction notes

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