Water → HCID 18519869, compound

HRID 1368067Notes

Reaction equation

HRID 1368067 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([C:8]1[NH:12][CH:11]=[C:10]([C:13](=[O:20])[CH2:14][N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH:9]=1)=[O:7].[CH3:25][S:26][CH2:27][CH2:28]Cl.O>CCCCCC.CN(C=O)C>[Cl:3][C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[C:6]([C:8]1[N:12]([CH2:25][S:26][CH2:27][CH3:28])[CH:11]=[C:10]([C:13](=[O:20])[CH2:14][N:15]([CH2:16][CH3:17])[CH2:18][CH3:19])[CH:9]=1)=[O:7]

Participants

7

Reactant 4

HCID 962WaterHCID 109652-Chloroethyl methyl sulfideHCID 24758Sodium hydrideHCID 18519857HCID 18519857, compound

Product 1

HCID 18519869HCID 18519869, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
65 °C

Procedure

0.2 g (0.0045 moles) of 60% NaH in oil was washed with hexane and 3 mL of DMF was added. To the suspension was added a solution dropwise of 1.2 g (0.0035 moles) of 1-[5-(2-chlorobenzoyl)-1H-pyrrol-3-yl]-2-(N,N-diethylamino)ethanone in 8 mL of DMF. After stirring for 10 m, 1.5 mL (0.0070 moles) of chloroethyl methyl sulfide was added and the reaction heated to 65° C. for 4 h. Water was added and extracted with Et2O, the organics were washed with water, brine and dried (Na2SO4). The solvent was evaporated in vacuo. The resulting oil was passed through a Biotage Flash 40 L, silica gel (97:3:0.1 CH2Cl2:MeOH:NH40H), then treated with ethereal HCl. After recrystallizing from 2-PrOH, 0.11 g of Compound 16; mp 157-158° C. CIMS m/z=393 (MH+). 1HNMR (300 MHz, DMSO-d6) δ 8.3 (Ar, 1H); 7.6-7.4 (Ar, 4H); 6.9 (Ar, 1H); 4.7 (m, 4H); 3.3(s,3H); 3.2 (m, 4H); 2.9 (m, 2H); 1.2 (t, 6H). Anal calc'd for C20H25CIN2O2S.HCl: C, 55.94; H, 6.1; N, 6.52. Found: C, 55.77, H, 6.12; N, 6.31.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionextracted with Et2O
  4. washthe organics were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was evaporated in vacuo
  7. additiontreated with ethereal HCl
  8. customAfter recrystallizing from 2-PrOH, 0.11 g of Compound 16

Sources & evidence

ORD record
ord-2b94a69877964d9499216acf3fd8018f
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

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