Phenyl chloroformate → HCID 58097294, compound

HRID 1514752Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([O:17][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20])=[C:13]([Cl:28])[CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:36]>C(OCC)(=O)C>[C:38]1([O:37][C:35](=[O:36])[NH:10][C:8]2[N:7]([C:11]3[CH:16]=[CH:15][C:14]([O:17][Si:18]([CH:19]([CH3:20])[CH3:21])([CH:22]([CH3:24])[CH3:23])[CH:25]([CH3:27])[CH3:26])=[C:13]([Cl:28])[CH:12]=3)[N:6]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:9]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of aminopyrazole of Example 2 (325 g, 0.707 moles) in ethyl acetate (1625 ml) under nitrogen, was added sodium bicarbonate aqueous solution (8% w/v, 1625 ml, 1.54 moles). Phenyl chloroformate (145 ml, 1.155 moles) was added over 15 minutes and stirred at 20° C. for 16 hours. The organic phase was separated and washed with water (1625 ml). Solvent was distilled under reduced pressure and replaced by n-heptane (1625 ml). The solution was cooled to 5° C. and granulated for 3 hours. The solid was collected by filtration to give the title compound as a white solid (368 g, 88%).

Workup

customThe organic phase was separated
washwashed with water (1625 ml)
distillationSolvent was distilled under reduced pressure
temperatureThe solution was cooled to 5° C.
waitgranulated for 3 hours
filtrationThe solid was collected by filtration

Sources & evidence

ORD record: ord-261843773cc848a0afff10f5c2621565
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08222273B2

Reaction notes

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