Dimethylformamide → HCID 21914394, compound

HRID 1245823Notes

Reaction equation

HRID 1245823 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.CN(C)C=O.[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[SH:29]>O>[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[S:29][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 805982-Bromobenzenethiol

Product 1

HCID 21914394HCID 21914394, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (10.95 g) and 2-chloroethylmorpholine hydrochloride (5.9 g) were mixed with dimethylformamide (50 ml) and 2-bromothiophenol was added before the mixture was heated to 100° C. for 3 days. The mixture was allowed to cool before water (500 ml) was added. The product was extracted into diethyl ether (×3). The combined extracts were dried over sodium sulphate and filtered before evaporation. The product was purified by column chromatography eluting with ethyl acetate/hexane mixtures to give a red/brown oil (6.024 g).

Workup

  1. additionwas added before the mixture
  2. additionwas added
  3. extractionThe product was extracted into diethyl ether (×3)
  4. dry with materialThe combined extracts were dried over sodium sulphate
  5. filtrationfiltered before evaporation
  6. customThe product was purified by column chromatography
  7. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-a5528d95520141d38fef408ec2153174
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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