Dimethyl Sulfoxide → HCID 11640089, compound

HRID 2425106Notes

Reaction equation

HRID 2425106 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[C:17]2[O:18][C:19]3[C:28]([CH3:29])=[CH:27][C:26]([CH2:30][OH:31])=[CH:25][C:20]=3[S:21](=[O:24])(=[O:23])[CH2:22][C:16]=2[CH:15]=[C:14]([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:13]=1.C(N(CC)CC)C>ClCCl>[Cl:11][C:12]1[C:17]2[O:18][C:19]3[C:28]([CH3:29])=[CH:27][C:26]([CH:30]=[O:31])=[CH:25][C:20]=3[S:21](=[O:23])(=[O:24])[CH2:22][C:16]=2[CH:15]=[C:14]([N:32]2[CH2:33][CH2:34][NH:35][CH2:36][CH2:37]2)[CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 131728531HCID 131728531, compound

Product 1

HCID 11640089HCID 11640089, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
22 °C

Procedure

DMSO (2.6 mL, 37.5 mmol) was added at −70° C. to a solution of oxalyl chloride (0.46 mL, 37.5 mmol) in dichloromethane (10 mL). Reaction mixture was stirred for 5 minutes and to this (4-chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cyclohepten-8-yl)-methanol (0.489 g, 1.19 mmol) [obtained by following the procedure described in Example 34] in dichloromethane (5 mL) was added. Reaction mixture was stirred for 5 minutes and to this triethylamine (8.4 mL, 62.5 mmol) was added. Reaction mixture was warmed to room temperature (22° C.) and stirred for 0.5 h. the reaction mixture was diluted with dichloromethane (200 mL), washed with water (100 mL), brine (50 mL) and dried over sodium sulphate. The crude product obtained was purified by column chromatography (silica gel, ethylacetate-pet ether) to obtain the title compound. Yield: 0.2 g (42%); 1H NMR (DMSO-d6, 300 MHz): δ 2.64 (s, 3H, CH3), 3.20 (s, 4H, 2CH2), 3.20 (s, 4H, 2CH2), 5.15 (s, 2H, CH2), 7.14 (d, 2H, Ar), 8.03 (s, 1H, Ar), 8.24 (s, 1H, Ar), 9.97 (s, 1H, CHO); MS: m/e (EI) 406 (M+).

Workup

  1. customReaction mixture
  2. customobtained
  3. additionwas added
  4. customReaction mixture
  5. additionwas added
  6. customReaction mixture
  7. washwashed with water (100 mL), brine (50 mL)
  8. dry with materialdried over sodium sulphate
  9. customThe crude product obtained
  10. customwas purified by column chromatography (silica gel, ethylacetate-pet ether)

Sources & evidence

ORD record
ord-4f8c5da3d6044103a42679b568255102
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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