HCID 23365500, compound → HCID 460351, compound

HRID 1080623Notes

Reaction equation

O.O.Br.Br.Br.Br.Br.Br.Br.Br.[F:11][C:12]1[C:17]([F:18])=[C:16]([CH2:19][N:20]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:15]([F:34])=[C:14]([F:35])[C:13]=1[CH2:36][N:37]1[CH2:50][CH2:49][CH2:48][NH:47][CH2:46][CH2:45][NH:44][CH2:43][CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1>C(O)(=O)C.Br>[F:35][C:14]1[C:15]([F:34])=[C:16]([CH2:19][N:20]2[CH2:33][CH2:32][CH2:31][NH:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:17]([F:18])=[C:12]([F:11])[C:13]=1[CH2:36][N:37]1[CH2:50][CH2:49][CH2:48][NH:47][CH2:46][CH2:45][NH:44][CH2:43][CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1

Participants

Conditions

Temperature: 100 °C

Procedure

1,1'-[2,3,5,6-Tetrafluoro-1,4-phenylenebis-(methylene)]-bis-tris-(p-toluenesulfonyl)-1,4,8,11-tetraazacyclotetradecane (200 mg, 0.13 mmol) was dissolved in a mixture of acetic acid and hydrobromic acid (48%) in a ratio of approximately 3:2 by volume (10 ml) and heated to 100° C. for 24 hours during which time a white solid precipitated. The mixture was allowed to cool and the solid was filtered off and washed with acetic acid and ether and dried in vacuo giving a white solid identified by 1H NMR, FAB-MS and elemental analysis as 1,1'-[2,-3,5,6-tetra-fluoro-1,4-phenylene-bis-(methylene)]-bis-1,4,8,11-tetraazacyclo-tetradecane octahydrobromide dihydrate (65 mg, 40%).

Workup

customprecipitated
temperatureto cool
filtrationthe solid was filtered off
washwashed with acetic acid and ether
customdried in vacuo
customgiving a white solid

Sources & evidence

ORD record: ord-d17ec9c15c9c40589fdcef0151062fbc
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05583131

Reaction notes

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