Benzoyl chloride, 3,4,5-trimethoxy- → HCID 21500228, compound

HRID 1729653Notes

Reaction equation

HRID 1729653 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].C([O-])(O)=O.[Na+].[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH:35]=[C:36]([O:40][CH3:41])[C:37]=1[O:38][CH3:39])[C:32](Cl)=[O:33]>CC(C)=O>[CH3:41][O:40][C:36]1[CH:35]=[C:31]([CH:30]=[C:29]([O:28][CH3:27])[C:37]=1[O:38][CH3:39])[C:32]([NH:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N:16]1[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1)[C:5]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:6])=[O:33]

Participants

5

Reactant 3

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516892Sodium BicarbonateHCID 1093516(3-Amino-4-morpholin-4-yl-phenyl)-phenyl-methanone

Product 1

HCID 21500228HCID 21500228, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

28 g. of 3-amino-4-morpholino-benzophenone are dissolved in 560 ml. of acetone, and 17 g. of solid sodium hydrocarbonate are added. A solution of 25.4 g. of 3,4,5-trimethoxybenzoyl chloride in 260 ml. of acetone are added dropwise to the solution at room temperature, under vigorous stirring. The temperature of the reaction mixture rises with about 6° to 10° C. After the addition the mixture is stirred for additional 30 minutes at room temperature, then poured into ice water. The separated product is filtered off, washed with water, dried, and crystallized from a mixture of acetone and ether. 37.5 g. of 3-(3,4,5-trimethoxybenzoylamino)-4-morpholino-benzophenone are obtained; m.p.: 171°-172° C.

Workup

  1. customrises with about 6° to 10° C
  2. additionAfter the addition the mixture
  3. filtrationThe separated product is filtered off
  4. washwashed with water
  5. customdried
  6. customcrystallized from a mixture of acetone and ether

Sources & evidence

ORD record
ord-8c13704777934ce0bf5c5d3e8caeb5d2
Source dataset
uspto-grants-1976_11
Patent number
US03989701

Reaction notes

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