2,5-Dimethyl-1,3-benzoxazol-6-amine → 2-Amino-5-(m-dioctadecylcarbamoylbenzenesulfonamido)-p-cresol hydrochloride

HRID 647226Notes

Reaction equation

HRID 647226 reaction equation
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][C:5]2[N:6]=C(C)[O:8][C:4]=2[CH:3]=1.[CH2:13]([N:31]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[C:32](=[O:43])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([S:39]([Cl:42])(=[O:41])=[O:40])[CH:34]=1)[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][CH3:30]>N1C=CC=CC=1.ClCCl>[ClH:42].[NH2:6][C:5]1[C:4]([OH:8])=[CH:3][C:2]([NH:1][S:39]([C:35]2[CH:36]=[CH:37][CH:38]=[C:33]([C:32](=[O:43])[N:31]([CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[CH2:13][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][CH3:30])[CH:34]=2)(=[O:41])=[O:40])=[C:11]([CH3:12])[CH:10]=1

Participants

5

Reactant 2

HCID 204858572,5-Dimethyl-1,3-benzoxazol-6-amineHCID 204858833-(Dioctadecylcarbamoyl)benzene-1-sulfonyl chloride

Product 1

HCID 204858602-Amino-5-(m-dioctadecylcarbamoylbenzenesulfonamido)-p-cresol hydrochlorideYield 90%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-amino-2,5-dimethylbenzoxazole (14.8 g, 0.1 mol) in 100 ml of pyridine and 500 ml of dichloromethane was added N,N-dioctadecyl-3-chlorosulfonylbenzamide (72.4 g, 0.1 mol). The mixture was stirred overnight and then washed with water, 10 percent aqueous hydrochloric acid and again with water. To the organic layer was added 10 ml of hydrochloric acid, 300 ml of water and 1000 ml of THF. The mixture was stirred overnight and the precipitate collected, washed with acetonitrile and nearly dried. The damp filter cake was placed in 2 liters of THF and 50 ml of concentrated hydrochloric acid and refluxed 2 hours. The mixture was concentrated to an oil and triturated with one liter of acetonitrile to yield 77.5 g (90 percent) of the product.

Workup

  1. washwashed with water, 10 percent aqueous hydrochloric acid and again with water
  2. additionTo the organic layer was added 10 ml of hydrochloric acid, 300 ml of water and 1000 ml of THF
  3. stirringThe mixture was stirred overnight
  4. customthe precipitate collected
  5. washwashed with acetonitrile
  6. customnearly dried
  7. temperature50 ml of concentrated hydrochloric acid and refluxed 2 hours
  8. concentrationThe mixture was concentrated to an oil
  9. customtriturated with one liter of acetonitrile

Sources & evidence

ORD record
ord-e48d67ee87cf4e0da7720534815dfd34
Source dataset
uspto-grants-1983_10
Patent number
US04407930

Reaction notes

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