Chloroacetyl chloride → 2-chloro-N-{3-[4-(4-isopropyl-phenyl)-2-oxo-6-propargyloxy-2H-quinazolin-1-ylmethyl]-phenyl}-acetamide

HRID 445175Notes

Reaction equation

HRID 445175 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]#[CH:19])=[CH:13][CH:14]=2)[C:9]([C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)=[N:8][C:7]1=[O:29].[Cl:33][CH2:34][C:35](Cl)=[O:36].C(N(CC)CC)C.O.C(Cl)Cl>C(Cl)Cl>[Cl:33][CH2:34][C:35]([NH:1][C:2]1[CH:32]=[CH:31][CH:30]=[C:4]([CH2:5][N:6]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]#[CH:19])=[CH:13][CH:14]=3)[C:9]([C:20]3[CH:25]=[CH:24][C:23]([CH:26]([CH3:27])[CH3:28])=[CH:22][CH:21]=3)=[N:8][C:7]2=[O:29])[CH:3]=1)=[O:36]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 21908982Water methylene chlorideHCID 451416231-(3-amino-benzyl)-4-(4-isopropyl-phenyl)-6-propargyloxy-1H-quinazolin-2-one

Product 1

HCID 451416242-chloro-N-{3-[4-(4-isopropyl-phenyl)-2-oxo-6-propargyloxy-2H-quinazolin-1-ylmethyl]-phenyl}-acetamideYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 200 mg (0.47 mmol) 1-(3-amino-benzyl)-4-(4-isopropyl-phenyl)-6-propargyloxy-1H-quinazolin-2-one in 3 ml CH2Cl2 is treated at 0° C. with 41 μl (0.52 mmol; 1.1 eq.) chloroacetyl chloride and 79 μl (0.57 mmol; 1.2 eq.) triethylamine. The mixture is allowed to come to rt. Extractive work-up with water/CH2Cl2 yields 225 mg (95%) of a yellow solid. m.p. 170-172° C.

Workup

  1. customto come to rt

Sources & evidence

ORD record
ord-8a0fc7913ed149bbb42727aa3cb98fbe
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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