Acetic Anhydride → HCID 59655395, compound

HRID 18840

Reaction equation

HRID 18840 reaction equation
Cl.[F:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][S:8][C:9]2[NH:10][C@H:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36]>CN(C)C1C=CN=CC=1.ClCCl>[F:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][S:8][C:9]2[N:13]([C:35](=[O:37])[CH3:36])[C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C@H:11]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 685688872-[(4-Fluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole Hydrochloride

Product 1

HCID 59655395HCID 59655395, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[(4-fluorobenzyl)thio]-cis-4,5-diphenyl-4,5-dihydro-1H-imidazole hydrochloride (197) (0.50 g, 1.25 mmol), triethylamine (0.384 mL, 2.75 mmol), 4-dimethylaminopyridine (20 mg) in dichloromethane (20 mL) is added acetic anhydride (0.130 mL, 1.38 mmol), and the mixture is stirred at rt for 3 h. Additional acetic anhydride (0.100 mL, 1.06 mmol) is added, and the mixture is stirred at rt overnight. The reaction mixture is diluted with dichloromethane and washed with water, brine, and the organic layer is dried (MgSO4), filtered, and evaporated. The residue is recrystallized from heptane:dichloromethane (95:5) to give 0.37 g of the product 549. 1H NMR (CDCl3) δ 7.60-7.40 (m, 2H), 7.10-6.90 (m, 8H), 6.90-6.75 (m, 2H), 6.75-6.65 (m, 2H), 5.65 (d, 1H), 5.43 (d, 1H), 4.33 (q, 2H), 1.91 (s, 3H). MS: m/z 405 (M++1).

Workup

  1. stirringthe mixture is stirred at rt overnight
  2. washwashed with water, brine
  3. dry with materialthe organic layer is dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is recrystallized from heptane:dichloromethane (95:5)

Sources & evidence

ORD record
ord-48e132940c824556bf81be1425ad37bc
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Linked notes

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