Tert-Butylamine → 5-Acetamino-1-acetoxynaphthalene-2-sulfonic acid-tert.-butylamide

HRID 326170

Reaction equation

HRID 326170 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[NH:6]([C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][C:14]([S:24](Cl)(=[O:26])=[O:25])=[C:15]2[O:20][C:21](=[O:23])[CH3:22])[C:7]([CH3:9])=[O:8]>CC(C)=O>[C:1]([NH:5][S:24]([C:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][CH:18]=[CH:19][C:10]=2[NH:6][C:7]([CH3:9])=[O:8])[C:15]=1[O:20][C:21](=[O:23])[CH3:22])(=[O:26])=[O:25])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 941252-Naphthalenesulfonyl chloride, 5-(acetylamino)-1-(acetyloxy)-

Product 1

HCID 204626025-Acetamino-1-acetoxynaphthalene-2-sulfonic acid-tert.-butylamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

14.5 g of t-butylamine in 50 ml of acetone were added dropwise to a solution of 18.8 g of the compound from stage 2 (0.55 mols) in 150 ml of acetone at -5° to 0° C. The mixture was further stirred overnight, filtered off from the deposit, concentrated and crystallized from ether with a little acetonitrile. Yield: 19.2 g=92% of the theoretical yield; mp: 203°-206° C.

Workup

  1. filtrationfiltered off from the deposit
  2. concentrationconcentrated
  3. customcrystallized from ether with a little acetonitrile

Sources & evidence

ORD record
ord-63164cbb022e4f2da28dbf9edfdf3a32
Source dataset
uspto-grants-1984_04
Patent number
US04444867

Linked notes

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