Hydrochloric Acid → HCID 178443209, compound

HRID 867899Notes

Reaction equation

HRID 867899 reaction equation
[CH2:1]([S:5]([NH:8][C:9]1[CH:29]=[CH:28][C:12]([O:13][CH:14]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:15](Cl)=[O:16])=[CH:11][CH:10]=1)(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].C([N:33]1[C:37]2=[CH:38][C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])=[N:40][N:36]2[C:35]([C:45]2[C:50]([CH3:51])=[CH:49][C:48]([CH3:52])=[C:47]([NH2:53])[C:46]=2[CH3:54])=[N:34]1)(=O)C.C(=O)(O)[O-].[Na+].[OH-].[K+].Cl.[CH2:63]1COC[CH2:64]1>O>[C:41]([C:39]1[CH:38]=[C:37]2[N:36]([N:40]=1)[C:35]([C:45]1[C:46]([CH3:54])=[C:47]([NH:53][C:15](=[O:16])[CH:14]([O:13][C:12]3[CH:28]=[CH:29][C:9]([NH:8][S:5]([CH2:1][CH2:2][CH2:3][CH3:4])(=[O:7])=[O:6])=[CH:10][CH:11]=3)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:63][CH3:64])[C:48]([CH3:52])=[CH:49][C:50]=1[CH3:51])=[N:34][NH:33]2)([CH3:44])([CH3:43])[CH3:42]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran3×HCID 14797Potassium HydroxideHCID 516892Sodium BicarbonateHCID 19967810HCID 19967810, compoundHCID 21288873HCID 21288873, compound

Product 1

HCID 178443209HCID 178443209, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(4-n-Butylsulfonamidophenoxy)-n-dodecanoyl chloride (16.6 g, 35 mmole) in THF (35 ml) was added to a suspension of the product of part (b) (11.9 g, 35 mmole) and sodium bicarbonate (4.2 g) in THF (95 ml). After 22 hours, more THF (45 ml) and potassium hydroxide (7.9 g, 140 mmole) in water (175 ml) were added and stirring continued for a further 80 minutes. 3M HCl (100 ml) was added and the THF removed by evaporation under reduced pressure. Dichloromethane (250 ml) was added and the organic extract separated, washed with saturated NaCl, (2×150 ml) dried and evaporated to give the product 23.7 g (92%) m.p. 117°-120° C.

Workup

  1. waitcontinued for a further 80 minutes
  2. customthe THF removed by evaporation under reduced pressure
  3. additionDichloromethane (250 ml) was added
  4. extractionthe organic extract
  5. customseparated
  6. washwashed with saturated NaCl, (2×150 ml)
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-756bfb3888e448a88b9ec6e6d6835b88
Source dataset
uspto-grants-1988_10
Patent number
US04777121

Reaction notes

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