HuagongsheHuagongshe Chemistry Print Report · For research reference only
Chloroacetyl chloride → 2-chloro-N-{3-[4-(4-isopropyl-phenyl)-2-oxo-6-propargyloxy-2H-quinazolin-1-ylmethyl]-phenyl}-acetamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Chloroacetyl chloride | HCID 6577 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Water methylene chloride | HCID 21908982 | — |
| Reactant | 1-(3-amino-benzyl)-4-(4-isopropyl-phenyl)-6-propargyloxy-1H-quinazolin-2-one | HCID 45141623 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-chloro-N-{3-[4-(4-isopropyl-phenyl)-2-oxo-6-propargyloxy-2H-quinazolin-1-ylmethyl]-phenyl}-acetamide | HCID 45141624 | 95.7% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08476286B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-8a0fc7913ed149bbb42727aa3cb98fbe |
| Source note | uspto-grants-2013_07 |