Toluene → HCID 86672021, compound

HRID 473858Notes

Reaction equation

HRID 473858 reaction equation
Cl.[S:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]3[O:16][CH2:15][CH2:14][NH:13][CH2:12][C:11]=3[CH:17]=2)=[CH:5][N:4]=[CH:3]1.[C:18](Cl)([Cl:20])=[O:19].C1(C)C=CC=CC=1.C(N(CC)CC)C>ClCCl>[S:2]1[C:6]([C:7]2[CH:8]=[CH:9][C:10]3[O:16][CH2:15][CH2:14][N:13]([C:18]([Cl:20])=[O:19])[CH2:12][C:11]=3[CH:17]=2)=[CH:5][N:4]=[CH:3]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 8471TriethylamineHCID 67513974HCID 67513974, compound

Product 1

HCID 86672021HCID 86672021, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 7-(thiazol-5-yl)-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine hydrochloride as obtained in step 2 in dichloromethane (20 mL) at −20° C. added 20% phosgene in toluene (0.25 mL, 0.50 mmol) followed by addition of triethylamine (0.35 mL, 25 mmol). The reaction was allowed to warm to 25° C. and stand for 18 h. The mixture was then concentrated to give 7-(thiazol-5-yl)-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carbonyl chloride.

Workup

  1. concentrationThe mixture was then concentrated

Sources & evidence

ORD record
ord-b9ac24f9f1f445768e02fd915c36076a
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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