Hydrochloric Acid → 2-[2'(2-Methoxyethoxy)-5'-nitrobenzenesulfonamido]-4-hexadecyloxy-5-methylphenol

HRID 2287013Notes

Reaction equation

HRID 2287013 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:6]([CH3:26])=[CH:5][C:4]=1[OH:27].[CH3:28][O:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[S:42](Cl)(=[O:44])=[O:43].O1CCCC1.Cl>N1C=CC=CC=1>[CH3:28][O:29][CH2:30][CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[S:42]([NH:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:6]([CH3:26])=[CH:5][C:4]=1[OH:27])(=[O:44])=[O:43]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 125250472-Amino-4-hexadecyloxy-5-methylphenol hydrochlorideHCID 129314372-(2-Methoxyethoxy)-5-nitrobenzenesulfonyl chloride

Product 1

HCID 127288472-[2'(2-Methoxyethoxy)-5'-nitrobenzenesulfonamido]-4-hexadecyloxy-5-methylphenol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20 g of 2-amino-4-hexadecyloxy-5-methylphenol hydrochloride and 18 g of 4-(2-methoxyethoxy)nitrobenzene-3-sulfonyl chloride prepared as described in Step (a) above were added to a mixture of 100 ml of tetrahydrofuran and 10 ml of pyridine and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added to a mixture of 300 ml of ice water and 50 ml of a 35% hydrochloric acid aqueous solution with stirring. The crystals thus-precipitated were recovered with filtration, washed with water, air-dried and recrystallized from 100 ml of acetonitrile. Yield: 35 g; Melting Point: 85.5° to 86° C.

Workup

  1. stirringwith stirring
  2. customThe crystals thus-precipitated
  3. filtrationwere recovered with filtration
  4. washwashed with water
  5. customair-dried
  6. customrecrystallized from 100 ml of acetonitrile

Sources & evidence

ORD record
ord-5a80551a70c04fa192a65cb1dc7bf68a
Source dataset
uspto-grants-1981_05
Patent number
US04268625

Reaction notes

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