1,2-Dichloroethane → HCID 68674801, compound

HRID 1993071Notes

Reaction equation

HRID 1993071 reaction equation
O[N:2]1C2C=CC=CC=2N=N1.C(Cl)CCl.[C:15]([O:19][C:20](=[O:50])[CH2:21][CH:22]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:35]=[C:36]([C:40]3[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=3)[CH:37]=[CH:38][CH:39]=2)=[CH:28][CH:27]=1)[C:23](O)=[O:24])([CH3:18])([CH3:17])[CH3:16].[OH-].[NH4+]>ClCCl>[C:15]([O:19][C:20](=[O:50])[CH2:21][CH:22]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:35]=[C:36]([C:40]3[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=3)[CH:37]=[CH:38][CH:39]=2)=[CH:28][CH:27]=1)[C:23]([NH2:2])=[O:24])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 68675946HCID 68675946, compound

Product 1

HCID 68674801HCID 68674801, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-hydroxybenzotriazole (225 mg, 1.65 mmol) and EDC (315 mg, 1.65 mmol) were added sequentially to compound 50.3 (750 mg, 1.5 mmol) in dichloromethane (25 mL). The resulting mixture was stirred for 1 h before ammonium hydroxide (25% in water, 630 mg, 4.5 mmol) was added dropwise. The reaction was quenched after 30 min. with water (10 mL). The reaction mixture was extracted with dichloromethane (10 mL×3). The organic extracts were combined, dried over MgSO4 and concentrated under reduced pressure. The product was purified via flash chromatography (50% ethyl acetate in hexanes) to yield 51.1 (720 mg) as a white solid. MS ESI (pos.) m/e: 500 (M+H). 1H NMR (400 MHz) (CDCl3) δ 7.72 (4H, s); 7.68 (1H, s); 7.57-7.48 (3H, m); 7.29-7.25 (2H, m); 7.0-6.97 (2H, d, J=6.8 Hz); 5.14 (2H, s); 3.91-3.88 (1H, m); 3.19-3.13 (1H, m); 2.60-2.55 (1H, m); 1.4 (9H, s).

Workup

  1. additionwas added dropwise
  2. customThe reaction was quenched after 30 min. with water (10 mL)
  3. extractionThe reaction mixture was extracted with dichloromethane (10 mL×3)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe product was purified via flash chromatography (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d602dfaebdae47c48f95644970eb1321
Source dataset
uspto-grants-2010_01
Patent number
US07649110B2

Reaction notes

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