Phosphorus oxychloride → HCID 18376562, compound

HRID 2300947Notes

Reaction equation

HRID 2300947 reaction equation
[Cl:1][C:2]1[C:6]([CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:5][S:4][C:3]=1[C:14]([O-:16])=O.[Na+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:35])[C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=2[NH2:34])=[CH:21][CH:20]=1.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:26](=[O:35])[C:27]2[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:28]=2[NH:34][C:14]([C:3]2[S:4][CH:5]=[C:6]([CH2:7][N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[C:2]=2[Cl:1])=[O:16])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 41860192-amino-5-chloro-N-(4-chlorophenyl)benzamideHCID 23701467Sodium 3-chloro4-(morpholin-4-yl)methyl-2-thiophene carboxylate

Product 1

HCID 18376562HCID 18376562, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of sodium 3-chloro-4-(morpholin-4-yl)methyl-2-thiophene carboxylate (1.0 g, 3.9 mmol) and N-(4-chlorophenyl)-2-amino-5-chlorobenzamide (0.88 g, 3.1 mmol) in pyridine (20 mL) at −10° C. was added POCl3 (0.40 mL, 4.3 mmol). After 45 minutes, the mixture was poured onto ice-water and the resulting solid collected by filtration. Crystallization from 1-butanol afforded 0.26 g (13% yield) of N-(4-chlorophenyl)-2-[((4-(morpholin-4-yl)methyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide, as a tan solid; NMR (DMSO-d6) 11.1 (s, 1), 10.8 (s, 1), 8.3 (d, 1), 7.9 (s, 1), 7.8 (s, 1), 7.7 (d, 2), 7.6 (d, 2), 7.4 (d, 3), 3.6 (s, 2), 3.3 (br, 4), 2.4 (br, 4) ppm.

Workup

  1. additionthe mixture was poured onto ice-water
  2. filtrationthe resulting solid collected by filtration
  3. customCrystallization from 1-butanol

Sources & evidence

ORD record
ord-dff18c0ad0704df1b55c22088d46e506
Source dataset
uspto-grants-2002_12
Patent number
US06498185B1

Reaction notes

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