Benzene → HCID 178445076, compound

HRID 1284050Notes

Reaction equation

HRID 1284050 reaction equation
[N:1]#[N:2].[S:3]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:27])[NH2:26])([C:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:11]([N:12]([CH3:14])[CH3:13])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:5])=[O:4].O.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([OH:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1.[CH:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(O)CCCCC>[N:1]#[N:2].[C:32]1([CH3:42])[CH:33]=[CH:34][C:35]([S:38]([OH:41])(=[O:39])=[O:40])=[CH:36][CH:37]=1.[C:32]1([CH3:42])[CH:33]=[CH:34][C:35]([S:38]([OH:41])(=[O:39])=[O:40])=[CH:36][CH:37]=1.[CH2:47]([O:29][C:28](=[O:30])[C@H:20]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:26])[NH2:27])[NH:19][S:3]([C:6]1[C:18]2[CH:17]=[CH:16][CH:15]=[C:11]([N:12]([CH3:13])[CH3:14])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:4])=[O:5])[CH2:48][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

5

Reactant 3

HCID 241BenzeneHCID 521998p-Toluenesulfonic acid monohydrateHCID 178482655HCID 178482655, compound

Product 1

HCID 178445076HCID 178445076, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 81031-HexanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1.0 gram of N2 -dansyl-L-arginine and 1.4 gram of p-toluenesulfonic acid monohydrate in 10 ml of n-hexyl alcohol was heated for 30 minutes at 100°C. To the thus obtained clear solution, 100 ml of benzene was added, and the mixture was refluxed for 3 hours, removing water by azeotropic distillation. After the solvent was removed by distillation, 50 ml of ethyl ether and 50 ml of petroleum ether were added to the residue to give a crystalline mass. Crystallization from acetone gave N2 -dansyl-L-arginine n-hexyl ester di(p-toluenesulfonate) in 95% yield; mp. 190°-193°C.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customremoving water
  3. distillationby azeotropic distillation
  4. customAfter the solvent was removed by distillation, 50 ml of ethyl ether and 50 ml of petroleum ether
  5. additionwere added to the residue
  6. customto give a crystalline mass
  7. customCrystallization from acetone

Sources & evidence

ORD record
ord-9ca6241f29f84b9ca07a2fa95c926968
Source dataset
uspto-grants-1976_08
Patent number
US03978045

Reaction notes

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