Triethylamine → HCID 21225906, compound

HRID 1060516Notes

Reaction equation

HRID 1060516 reaction equation
S(Cl)(Cl)(=O)=O.[N-:6]=[N+:7]=[N-:8].[N-:9]=[N+:10]=[N-:11].[C:12]1(=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[CH:14]=[CH:13]1.C(N(CC)CC)C>O1CCOCC1>[N-:6]=[N+:7]=[N-:8].[N-:9]=[N+:10]=[N-:11].[C:15]1(=[O:22])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:12](=[O:23])[CH:13]=[CH:14]1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 21917475HCID 21917475, compound

Product 1

HCID 21225906HCID 21225906, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
40 °C

Procedure

10.1 g (0.05 mol) of 4,4-dihydroxydiphenyl ether (result of calculation of dipole moment based on MOPAC-97=0.73 debye) and 47.0 g (0.175 mol) of 4-naphthoquinone diazide sulphonyl chloride were dissolved in 500 g of 1,4-dioxane under a current of dry nitrogen, and then warmed to 40° C. To this there was added, dropwise, 17.7 g (0.175 mol) of triethylamine mixed with 50 g of 1,4-dioxane, in such a way that the internal temperature of the system did not rise to more than 45° C. Following the dropwise addition, stirring was carried out for 2 hours at 40° C. The by-product triethylamine hydrochloride was filtered off and the filtrate poured into 3 litres of 1% hydrochloric acid, after which the precipitate which was deposited was collected by filtering. Washing was carried out twice with 10 litres of water, and drying performed for 20 hours in a vacuum dryer at 50° C. Naphthoquinone diazide compound (1) was obtained. (On average, 1.75 of the Q groups=4-naphthoquinone diazide sulphonyl groups and 0.25=hydrogen.)

Workup

  1. additionTo this there was added
  2. customdid not rise to more than 45° C
  3. additionthe dropwise addition
  4. filtrationThe by-product triethylamine hydrochloride was filtered off
  5. additionthe filtrate poured into 3 litres of 1% hydrochloric acid
  6. customafter which the precipitate which was deposited was collected
  7. filtrationby filtering
  8. washWashing
  9. customdrying
  10. waitperformed for 20 hours in a vacuum dryer at 50° C

Sources & evidence

ORD record
ord-03c0a5118836486584618f04e9d2f36a
Source dataset
uspto-grants-2003_02
Patent number
US06524764B1

Reaction notes

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