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1,2-Dichloroethane → HCID 68676353, compound

HRID 1993069
Notes
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Reaction equation

HRID 1993069 reaction equation
[C:1]([O:5][C:6](=[O:36])[CH2:7][CH:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:21]=[C:22]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)[CH:23]=[CH:24][CH:25]=2)=[CH:14][CH:13]=1)[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.C(Cl)CCl.[CH3:51][NH:52][CH3:53]>ClCCl>[C:1]([O:5][C:6](=[O:36])[CH2:7][CH:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[CH:21]=[C:22]([C:26]3[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=3)[CH:23]=[CH:24][CH:25]=2)=[CH:14][CH:13]=1)[C:9]([N:52]([CH3:53])[CH3:51])=[O:10])([CH3:4])([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 757711-HydroxybenzotriazoleHCID 68675946HCID 68675946, compound

Product 1

HCID 68676353HCID 68676353, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

A solution of compound 50.3 (50 mg, 0.1 mmol) in dichloromethane (2 mL) was treated with 1-hydroxybenzotriazole (15 mg, 0.11 mmol) and EDC (21 mg, 0.11 mmol) sequentially. The resulting mixture was stirred for 1 h. before dimethylamine (9 mg, 0.2 mmol) was added dropwise. The reaction was quenched 30 min. later with water (5 mL). The reaction mixture was extracted with dichloromethane (2 mL×3). The organic extracts were combined, dried over MgSO4 and concentrated under reduced pressure to yield amide 50.4 (48 mg). The product was used in the next step without further purification. MS ESI (pos.) m/e: 527 (M+).

Workup

  1. additionwas added dropwise
  2. customThe reaction was quenched 30 min. later with water (5 mL)
  3. extractionThe reaction mixture was extracted with dichloromethane (2 mL×3)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7c67c0cc9a4486092e66b40cd927b93
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07649110B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes