Dioctadecylamine → 3-(Dioctadecylcarbamoyl)benzene-1-sulfonyl chloride

HRID 647230Notes

Reaction equation

HRID 647230 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].[CH2:14]([NH:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].C(N(CC)C(C)C)(C)C>C1COCC1>[CH2:33]([N:32]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:8](=[O:9])[C:7]1[CH:11]=[CH:12][CH:13]=[C:5]([S:2]([Cl:1])(=[O:4])=[O:3])[CH:6]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]

Participants

5

Reactant 3

HCID 66989DioctadecylamineHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-HCID 81531Diisopropylethylamine

Product 1

HCID 204858833-(Dioctadecylcarbamoyl)benzene-1-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-chlorosulfonylbenzoyl chloride (25.0 g, 1.1406 mol) in 250 ml of THF at 0° C. was added in one portion a cold suspension of dioctadecylamine (59.3 g, 0.1137 mol) and N,N-diisopropylethylamine (13.5 g, 0.1406 mol) in 500 ml of THF. The addition was exothermic to ≃10° C. The reaction was stirred without cooling overnight. The white insolubles were filtered and the filtrate poured into dilute hydrochloric acid. The aqueous mixture was extracted with ethyl acetate and the organic layer washed with water, dried over anhydrous magnesium sulfate and concentrated to dryness under aspirator pressure at 35° C. The resulting 68 g (90 percent) of yellow oil slowly crystallized. NMR was consistent for the product.

Workup

  1. additionThe addition
  2. customto ≃10° C
  3. temperaturewithout cooling overnight
  4. filtrationThe white insolubles were filtered
  5. additionthe filtrate poured into dilute hydrochloric acid
  6. extractionThe aqueous mixture was extracted with ethyl acetate
  7. washthe organic layer washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated to dryness under aspirator pressure at 35° C
  10. customThe resulting 68 g (90 percent) of yellow oil slowly crystallized

Sources & evidence

ORD record
ord-17b9043e4bbd4f1b9dd977bea4785db9
Source dataset
uspto-grants-1983_10
Patent number
US04407930

Reaction notes

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