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

Triethylamine → Methyl 5-bromo-2-(2-(3-chlorophenyl)acetamido)benzoate

HRID 627540
Notes
Print preview

Reaction equation

HRID 627540 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].[Cl:20][C:21]1[CH:22]=[C:23]([CH2:27][C:28](Cl)=[O:29])[CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Br:19][C:16]1[CH:17]=[CH:18][C:9]([NH:8][C:28](=[O:29])[CH2:27][C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[CH:22]=2)=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 736224Methyl 2-amino-5-bromobenzoateHCID 106552492-(3-chlorophenyl)acetyl Chloride

Product 1

HCID 86716102Methyl 5-bromo-2-(2-(3-chlorophenyl)acetamido)benzoate

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (18 mL, 130 mmol) was added to methyl 2-amino-5-bromobenzoate (25 g, 110 mmol) in DCM (150 mL). The mixture was cooled to 0° C. and 2-(3-chlorophenyl)acetyl chloride (24.3 g, 130 mmol) in DCM (100 mL) was added. The mixture was allowed to warm to room temperature overnight with stirring. Aqueous K2CO3 (10 wt. %) was added and the mixture was extracted with DCM. The organic phase was dried (MgSO4), filtered, and concentrated to yield the title compound.

Workup

  1. temperatureto warm to room temperature overnight
  2. extractionthe mixture was extracted with DCM
  3. dry with materialThe organic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f59a3a9831294fa1a62836be685027d6
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309222B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes