2-Thiophenesulfonyl chloride → N-(4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide

HRID 1258372Notes

Reaction equation

HRID 1258372 reaction equation
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([OH:13])=[CH:5][CH:4]=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[S:19](Cl)(=[O:21])=[O:20]>C(N(CC)CC)C>[OH:13][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([NH:2][S:19]([C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)(=[O:21])=[O:20])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 855182-Thiophenesulfonyl chlorideHCID 27238584-Amino-1-naphthol hydrochloride

Product 1

HCID 697391N-(4-hydroxynaphthalen-1-yl)thiophene-2-sulfonamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

1.957 g 4-aminonaphth-1-ol hydrochloride salt was suspended in 80 ml dichloromethylene, to which at 0° C. was added 3.0 ml triethylamine. The suspension became a dark brown solution. To the solution was added 1.827 g thiophene-2-sulfonyl chloride. The mixture was stirred at r.t. overnight. The reaction mixture was diluted with dichloromethylene to 200 ml and washed with 1N HCl solution (30 ml×3), water (30 ml×3) and brine (30 ml). Dried over MgSO4, the organic phase was filtered and the filtrate was concentrated to dryness. The crude product was suspended in 50% methanol/H2O and filtered. The solid was washed with 50% methanol/H2O affording 2.7 g (90%) brown solid, m.p.: 146-148° C.

Workup

  1. customwas suspended in 80 ml dichloromethylene, to which at 0° C.
  2. additionThe reaction mixture was diluted with dichloromethylene to 200 ml
  3. washwashed with 1N HCl solution (30 ml×3), water (30 ml×3) and brine (30 ml)
  4. dry with materialDried over MgSO4
  5. filtrationthe organic phase was filtered
  6. concentrationthe filtrate was concentrated to dryness
  7. filtrationfiltered
  8. washThe solid was washed with 50% methanol/H2O affording 2.7 g (90%) brown solid, m.p.: 146-148° C.

Sources & evidence

ORD record
ord-fb0d27db65e44155bb69d62528c72e08
Source dataset
uspto-grants-2013_06
Patent number
US08466157B2

Reaction notes

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