Dimethylformamide → HCID 15295337, compound

HRID 128577Notes

Reaction equation

HRID 128577 reaction equation
[S:1]1(=[O:15])(=[O:14])[C:6]2[S:7][C:8]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:9][C:5]=2[CH:4]=[N:3][NH:2]1.[H-].[Na+].Cl.Cl[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[CH3:28]N(C=O)C>Cl>[N:22]1([CH2:21][CH2:20][N:2]2[N:3]=[C:4]([CH3:28])[C:5]3[CH:9]=[C:8]([S:10]([NH2:13])(=[O:11])=[O:12])[S:7][C:6]=3[S:1]2(=[O:14])=[O:15])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 19374697HCID 19374697, compound

Product 1

HCID 15295337HCID 15295337, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

The product from step C Example 1 (2.83 g, 10.07 mmol) was dissolved in DMF (40 mL). Sodium hydride (1.2 g, 30.21 mmol of a 60% suspension in mineral oil) was added slowly at room temperature. The mixture was stirred for 15 min and then chloroethylmorpholine hydrochloride salt (3.74 g, 20.14 mmol) was added. The mixture was warmed to 70° C. and stirred for 1h. DMF was evaporated under high vacuum. The residue obtained was diluted with 1N-HCl (50 mL) and washed with ethyl acetate (2×50 mL). The aqueous layer was neutralized with aqueous solution bicarbonate and extracted with ethyl acetate (3×50 mL). The combined ethyl acetate fractions were dried over MgSO4 and evaporated to provide a solid, repeated recrystallization from ethyl acetate-hexane yielded 1.35 g, (71%). mp: 160°-162° C. 1H NMR (DMSO-d6): δ: 2.38 (3H, s, CH3); 2.50 (4H, m, 2CH2N); 2.64 (2H, t, CH2); 3.50 (4H, m, 2CH2O); 4.01 (2H, t, CH2); 7.94 (1H, 1s, CH); 8.22 (2H, s, NH2 exchangeable). Analysis calculated for C12H18N4O5S3 -0.15 Ethyl acetate: C, 37.12; H, 4.74; N, 13.74. Found: C, 37.10; H, 4.79; N, 13.90.

Workup

  1. stirringstirred for 1h
  2. customDMF was evaporated under high vacuum
  3. customThe residue obtained
  4. washwashed with ethyl acetate (2×50 mL)
  5. extractionextracted with ethyl acetate (3×50 mL)
  6. dry with materialThe combined ethyl acetate fractions were dried over MgSO4
  7. customevaporated
  8. customto provide a solid
  9. customrecrystallization from ethyl acetate-hexane
  10. customyielded 1.35 g, (71%)

Sources & evidence

ORD record
ord-8c46379e433b47d186f142abc8957245
Source dataset
uspto-grants-1995_11
Patent number
US05464831

Reaction notes

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