Sulfamic Acid → HCID 57589042, compound

HRID 1782758Notes

Reaction equation

HRID 1782758 reaction equation
[C:1]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][C:20]=3[CH:30]=[O:31])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.C1C[O:41]CC1.Cl([O-])=O.[Na+].S(=O)(=O)(O)N>O>[C:1]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:2]=[CH:3][C:4]([CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:29]=[CH:28][C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][C:20]=3[C:30]([OH:41])=[O:31])=[CH:13][CH:14]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 8028TetrahydrofuranHCID 23668197Sodium ChloriteHCID 57589155HCID 57589155, compound

Product 1

HCID 57589042HCID 57589042, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

3.10 g (6.28 mmol) of ethyl 4-{3-[4-(1,1′-biphenyl-4-ylmethoxy)phenyl]propoxy}-3-formylbenzoate are introduced into 50 ml of THF. At about 0° C. (internal temperature), solutions of 2.13 g (18.8 nmol) of sodium chlorite in 2.5 ml of water and 1.83 g (18.8 mmol) of sulphamic acid in 9 ml of water are simultaneously added dropwise. The mixture is then stirred at 0° C. for 15 minutes. The reaction mixture is added to 120 ml of water and extracted with ethyl acetate (four times 60 ml). The combined organic phases are washed with saturated sodium chloride solution (twice 50 ml). A finely dispersed precipitate is evident in the organic phase. 300 ml of dichloromethane are added, and the solution is dried over sodium sulphate and concentrated. The resulting product (2.96 g) is reacted without further purification.

Workup

  1. extractionextracted with ethyl acetate (four times 60 ml)
  2. washThe combined organic phases are washed with saturated sodium chloride solution (twice 50 ml)
  3. addition300 ml of dichloromethane are added
  4. dry with materialthe solution is dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe resulting product (2.96 g) is reacted without further purification

Sources & evidence

ORD record
ord-348c7664cc3549788635a54d1e6885a4
Source dataset
uspto-grants-2009_03
Patent number
US07498460B2

Reaction notes

Loading…