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

Acetyl chloride → N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)acetamide

HRID 404269
Notes
Print preview

Reaction equation

HRID 404269 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:10])[CH3:9].[Br:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH2:27][CH:28]([OH:39])[CH2:29][NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=3)[C:18]3[C:23]([C:24]=2[CH:25]=1)=[CH:22][C:21]([Br:26])=[CH:20][CH:19]=3.C([Sn](=O)CCCC)CCC>C1(C)C=CC=CC=1>[Br:26][C:21]1[CH:20]=[CH:19][C:18]2[N:17]([CH2:27][CH:28]([OH:39])[CH2:29][N:30]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][CH3:38])[CH:32]=3)[C:8](=[O:10])[CH3:9])[C:16]3[C:24]([C:23]=2[CH:22]=1)=[CH:25][C:13]([Br:12])=[CH:14][CH:15]=3
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 61221Dibutyltin oxideHCID 3103961P7C3-OMe

Product 1

HCID 46853445N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-hydroxypropyl)-N-(3-methoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
150 °C

Procedure

Following a literature procedure (Morcuende, A.; Ors, M.; Valverde, S.; Herradón, B. J. Org. Chem. 1996, 5264-5270) triethylamine (14 Tl, 0.10 mmol) and acetyl chloride (8 Tl, 0.11 mmol) were added to a heterogeneous mixture of 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol (53 mg, 0.11 mmol) and dibutyltin oxide (5.5 mg, 0.022 mmol) in anhydrous toluene (1.5 ml). The reaction vessel was purged with nitrogen, sealed and heated under microwave radiation to 150° C. for 9 minutes. The reaction was monitored by lc/ms and all SM had been consumed. The heterogeneous solution was filtered under vacuum to yield a white solid. The crude product was used without purification.

Workup

  1. customThe reaction vessel was purged with nitrogen
  2. customsealed
  3. customhad been consumed
  4. filtrationThe heterogeneous solution was filtered under vacuum
  5. customto yield a white solid
  6. customThe crude product was used without purification

Sources & evidence

ORD record
ord-8e9624f6dfbe4f629006b72ba60d7a2a
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748473B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes