1,2-Dichloroethane → Ammonia methanol

HRID 1350452Notes

Reaction equation

HRID 1350452 reaction equation
[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]=[C:5]([N:16]3[CH2:21][CH2:20][NH:19][C@@H:18]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:17]3)[C:4]=2[N:3]=1.C=O.[C:32](O[BH-](OC(=O)C)OC(=O)C)(=[O:34])C.[Na+].[C:46](=O)(O)[O-:47].[Na+].[Cl:51][CH2:52]CCl>>[NH3:3].[CH3:32][OH:34].[OH2:47].[ClH:51].[ClH:51].[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]=[C:5]([N:16]3[CH2:21][CH2:20][N:19]([CH3:46])[C@@H:18]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:17]3)[C:4]=2[N:3]=1.[CH3:1][C:2]1[S:11][C:10]2[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[N:6]=[C:5]([N:16]3[CH2:21][CH2:20][N:19]([CH3:52])[C@@H:18]([CH2:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH2:17]3)[C:4]=2[N:3]=1.[ClH:51].[ClH:51]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 136005551HCID 136005551, compound

Product 2

HCID 21705897Ammonia methanolHCID 137194526(S)-2-Methyl-10-(4-methyl-3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene dihydrochloride hemihydrate

Procedure

Combine (S)-2-methyl-10-(3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene (0.5 g, 1.24 mmol) and 37% Formaldehyde solution (0.1 mL, 1.36 mmol)in 1,2-dichloroethane (25 mL). Stir for 10 minutes and add sodium triacetoxy borohydride (0.394, 1.86 mmol). Stir an additional 30 minutes and then pour solution onto saturated Sodium bicarbonate solution. Extract with methylene chloride to give 0.52 g of the crude product. Silica gel chromatography, eluting with methylene chloride: 2N NH3/methanol (100:3), gives 0.296 g of the title compound as the free base. The dihydrochloride salt precipitates in ethyl acetate as a yellow solid: mp 220° C.; mass spectrum (ion spray): m/z=418 (M+1); Analysis for C24H29Cl2N5S(0.5 H2O): calcd: C, 57.71; H, 6.05; N, 14.02; found: C, 57.81; H, 6.08; N, 13.81.

Workup

  1. stirringStir an additional 30 minutes
  2. extractionExtract with methylene chloride
  3. customto give 0.52 g of the crude product
  4. washSilica gel chromatography, eluting with methylene chloride

Sources & evidence

ORD record
ord-9b9c5195187045e2886a0ff8be48f25e
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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