4-Chlorobenzoyl chloride → HCID 131711131, compound

HRID 866320Notes

Reaction equation

HRID 866320 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][NH:14][CH2:15][C:16]([NH2:18])=[O:17].[Cl:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>C(Cl)(Cl)Cl>[ClH:20].[NH2:18][C:16](=[O:17])[CH2:15][N:14]([CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[O:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:19])[C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([Cl:20])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 85014-Chlorobenzoyl chlorideHCID 12878609HCID 12878609, compound

Product 1

HCID 131711131HCID 131711131, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Ten grams of 2-[[[2-[3-(Dimethylamino)propoxy]-phenyl]methyl]amino]acetamide (see Example 2B) and 7.1 g of p-chlorobenzoyl chloride are reacted in 110 ml of chloroform as described in Example 1. The finely-divided, solid product separates at the end of the addition; crude yield, after standing for about 16 hours at room temperature, 10.2 g; melting point 195°-197° C dec, sintering at 175° C. Work-up of the mother liquor does not yield any additional product. Following crystallization (of 9.7 g) from 50 ml of warm methanol - 100 ml of ether, the material weighs 6.3 g; melting point 198°-200° C, dec, sintering at 175° C.

Workup

  1. additionThe finely-divided, solid product separates at the end of the addition
  2. customcrude yield
  3. customsintering at 175° C
  4. customdoes not yield any additional product
  5. customcrystallization (of 9.7 g) from 50 ml of warm methanol - 100 ml of ether
  6. customsintering at 175° C.

Sources & evidence

ORD record
ord-930b9b0c391e4bd68c18b59e2af6b747
Source dataset
uspto-grants-1978_07
Patent number
US04098789

Reaction notes

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