Hydrochloric Acid → HCID 21435514, compound

HRID 2398504Notes

Reaction equation

HRID 2398504 reaction equation
[CH2:1]([N:8]([CH2:42][CH:43]([C:45]1[CH:50]=[CH:49][C:48]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[C:47]([CH2:59][NH2:60])[CH:46]=1)[OH:44])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:16][CH:17]([OH:34])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:20]([CH2:32][NH2:33])[CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:61][S:62](Cl)(=[O:64])=[O:63].Cl>N1C=CC=CC=1>[CH2:35]([N:15]([CH2:16][CH:17]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[C:20]([CH2:32][NH:33][S:62]([CH3:61])(=[O:64])=[O:63])[CH:19]=1)[OH:34])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:42][CH:43]([OH:44])[C:45]1[CH:50]=[CH:49][C:48]([O:51][CH2:52][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=2)=[C:47]([CH2:59][NH:60][S:62]([CH3:61])(=[O:64])=[O:63])[CH:46]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 21435504HCID 21435504, compound

Product 1

HCID 21435514HCID 21435514, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 9.35 g. of N,N'-dibenzyl-N,N'-bis[2-(3-aminomethyl-4-benzyloxyphenyl)-2-hydroxyethyl]-hexamethylenediamine in 50 ml. of pyridine is added 2.5 ml. of methanesulfonyl chloride at room temperature. After 18 hours the reaction mixture is added to an excess of 2N hydrochloric acid and extracted with chloroform. The extract is neutralized with sodium bicarbonate, washed, dried and evaporated to give N,N'-dibenzyl-N,N'-bis[2-(4-benzyloxy-3-methanesulfonamidomethylphenyl)-2-hydroxyethyl]-hexamethylenediamine. The latter, as the dihydrochloride, is hydrogenated with palladium-on-carbon to yield N,N'-bis[2-(4-hydroxy-3-methanesulfonamidomethylphenyl)-2-hydroxyethyl]-hexamethylenediamine dihydrochloride.

Workup

  1. customat room temperature
  2. extractionextracted with chloroform
  3. washwashed
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-0e3a89da2ef243818ac1e27dfdf221eb
Source dataset
uspto-grants-1977_05
Patent number
US04024281

Reaction notes

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