Triethylamine → HCID 86737297, compound

HRID 904311Notes

Reaction equation

HRID 904311 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([OH:29])[CH2:10][O:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:15][C:14](=[O:22])[C:13]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:37][O:38][C:39]1[CH:40]=[C:41]([CH:45]=[C:46]([O:50][CH3:51])[C:47]=1[O:48][CH3:49])[C:42](Cl)=[O:43]>C(Cl)(Cl)Cl>[C:23]1([C:13]2[C:14](=[O:22])[O:15][C:16]3[C:21]([C:12]=2[O:11][CH2:10][CH:9]([O:29][C:42](=[O:43])[C:41]2[CH:40]=[C:39]([O:38][CH3:37])[C:47]([O:48][CH3:49])=[C:46]([O:50][CH3:51])[CH:45]=2)[CH2:8][N:5]2[CH2:6][CH2:7][O:2][CH2:3][CH2:4]2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 23334041HCID 23334041, compound

Product 1

HCID 86737297HCID 86737297, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

14.2 g. (0.034 mol) of 4-(3'-morpholino-2'-hydroxypropoxy)-3-phenyl-coumarin hydrochloride (Example 32) are placed in 130 ml. of chloroform containing 3.4 g. (0.034 mol) of triethylamine. A solution of 7.83 g. (0.034 mol) of 3,4,5-trimethoxy-benzoyl chloride in 20 ml. of chloroform are then added in 21/2 hours. The mixture is then brought over 2 hours to 40°-50° C. Cooling takes place, the insoluble substance is filtered off, the filtrate is washed with a sodium bicarbonate solution and dried over sodium sulphate. The solvent is evaporated under vacuum and there are obtained 14.3 g. of an oil which cannot be crystallised. Yield 73.4% (theoretical yield 19.5 g.).

Workup

  1. temperatureCooling
  2. filtrationthe insoluble substance is filtered off
  3. washthe filtrate is washed with a sodium bicarbonate solution
  4. dry with materialdried over sodium sulphate
  5. customThe solvent is evaporated under vacuum and there
  6. customare obtained 14.3 g
  7. customof an oil which cannot be crystallised

Sources & evidence

ORD record
ord-cf5195bfa3344bc68085eff2f09a8e40
Source dataset
uspto-grants-1980_10
Patent number
US04230850

Reaction notes

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