Dimethylformamide → HCID 178501117, compound

HRID 550178Notes

Reaction equation

HRID 550178 reaction equation
ClS([N:5]=C=O)(=O)=O.[CH3:8][O:9][C:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18](O)=O)[CH2:14][CH2:13]1)=[O:11].CN(C=O)C>C(Cl)Cl>[C:18]([C@H:15]1[CH2:16][CH2:17][C@H:12]([C:10]([O:9][CH3:8])=[O:11])[CH2:13][CH2:14]1)#[N:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70918Chlorosulfonyl isocyanateHCID 178501163HCID 178501163, compound

Product 1

HCID 178501117HCID 178501117, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Chlorosulfonyl isocyanate (1.0 mL, 0.012 mol) was added to a solution of trans-4-(methoxycarbonyl)cyclohexanecarboxylic acid (2.00 g, 0.0107 mol) in DCM cooled to 0° C. The resulting solution was heated at reflux for 15 minutes and then cooled 0° C. and treated dropwise with DMF. The mixture was stirred at room temperature overnight then poured onto ice water and the organic phase separated and washed with a saturated solution of sodium bicarbonate. The solvent was removed in vacuo and the crude material was taken up in ethyl acetate, washed with 1N aq. NaOH (10 mL) and the ethyl acetate removed in vacua. The resulting crude product was used in subsequent steps without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.36-1.70 (4 H, m), 2.01-2.18 (4 H, m), 2.24-2.54 (2 H, m) and 3.68 (3 H, s).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 15 minutes
  3. temperaturecooled 0° C.
  4. additionthen poured onto ice water
  5. customthe organic phase separated
  6. washwashed with a saturated solution of sodium bicarbonate
  7. customThe solvent was removed in vacuo
  8. washwashed with 1N aq. NaOH (10 mL)
  9. customthe ethyl acetate removed in vacua
  10. customThe resulting crude product was used in subsequent steps without further purification

Sources & evidence

ORD record
ord-bacddc511db14040a8bb187d61822066
Source dataset
uspto-grants-2011_05
Patent number
US07943767B2

Reaction notes

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