Benzene → HCID 178482656, compound

HRID 903392Notes

Reaction equation

HRID 903392 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.C1C=CC=CC=1.[Cl:49][CH2:50][CH2:51][CH2:52]O>>[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.[Cl:49][CH2:50][CH2:51][CH2:52][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]

Participants

5

Reactant 4

HCID 241BenzeneHCID 123133-Chloro-1-propanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 178482655HCID 178482655, compound

Product 1

HCID 178482656HCID 178482656, compoundYield 88%

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 3-chloro-1-propanol 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 5 hours, removing water by azeotropic distillation. After the solvent was removed by distillation, 100 ml of ethyl ether was added to the residue to give a crystalline mass. Crystallization from acetone gave N2 -dansyl-L-arginine 3-chloropropyl ester di(p-toluenesulfonate) in 88% yield; mp. 140°-145° C.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customremoving water
  3. distillationby azeotropic distillation
  4. customAfter the solvent was removed by distillation, 100 ml of ethyl ether
  5. additionwas added to the residue
  6. customto give a crystalline mass
  7. customCrystallization from acetone

Sources & evidence

ORD record
ord-d7ec4bc9dfb446ad8c2325fea0e0c379
Source dataset
uspto-grants-1980_10
Patent number
US04227006

Reaction notes

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