HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ammonium Chloride → HCID 86591098, compound

HRID 1007311
Notes
Print preview

Reaction equation

HRID 1007311 reaction equation
C[Al](C)C.[Cl-].[NH4+:6].[C:7]1([C:13]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:14]2[CH:18]=[C:17]([C@@H:19]3[CH2:21][C@H:20]3[C:22]#[N:23])[N:16]=[CH:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[C:30]1([C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:14]2[CH:18]=[C:17]([C@@H:19]3[CH2:21][C@H:20]3[C:22](=[NH:6])[NH2:23])[N:16]=[CH:15]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 69872359HCID 69872359, compound

Product 1

HCID 86591098HCID 86591098, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×
HCID 6212
Chloroform
Solvent

Conditions

Temperature
25 °C

Procedure

A solution of trimethylaluminium in toluene (2M, 0.6 mL, 1.2 mmol) was slowly added to a suspension of ammonium chloride (64 mg, 12 mmol) in dry toluene (5 mL) at 0° C. under nitrogen. The resulting mixture was warmed to 25° C. and stirred for 3 hours until gas evolution had ceased. Then, N-triphenylmethyl-4-(trans-2-cyano-cyclopropyl)imidazole (200 mg, 0.53 mmol) in dry toluene (10 mL) was added and the reaction mixture was heated to 80° C. for 18 hours under nitrogen, slowly poured into a slurry of silica gel (15 g) in chloroform (50 mL), and stirred for 10 minutes. The silica was filtered and washed with methanol. The combined solvent mixture was concentrated under vacuum and the residue was purified on a silica gel column using 85/15/5 (v/v/v) methylene chloride/methanol/ammonium hydroxide as the eluent to give a white solid (140 mg, 68% yield).

Workup

  1. temperaturethe reaction mixture was heated to 80° C. for 18 hours under nitrogen
  2. stirringstirred for 10 minutes
  3. filtrationThe silica was filtered
  4. washwashed with methanol
  5. concentrationThe combined solvent mixture was concentrated under vacuum
  6. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-1ab57edb8e72427ba7178d5477a07a0c
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06794405B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes