Dichloromethane → HCID 18548707, compound

HRID 1266893Notes

Reaction equation

HRID 1266893 reaction equation
O[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:9]=[C:10]([C:14]3[CH2:20][C:19](=[O:21])[NH:18][C:17]4[CH:22]=[C:23]([N:26]5[CH:30]=[CH:29][CH:28]=[CH:27]5)[CH:24]=[CH:25][C:16]=4[N:15]=3)[CH:11]=[CH:12][CH:13]=2)[O:6][CH:7]=1.C(Cl)[Cl:32]>S(Cl)(Cl)=O>[Cl:32][CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:9]=[C:10]([C:14]3[CH2:20][C:19](=[O:21])[NH:18][C:17]4[CH:22]=[C:23]([N:26]5[CH:30]=[CH:29][CH:28]=[CH:27]5)[CH:24]=[CH:25][C:16]=4[N:15]=3)[CH:11]=[CH:12][CH:13]=2)[O:6][CH:7]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 18548762HCID 18548762, compound

Product 1

HCID 18548707HCID 18548707, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 4-[3-(4-hydroxymethyl-oxazol-2-yl)-phenyl]-8-pyrrol-1-yl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (Example 26) (1.0 g) in CH2Cl2 (15 mL) and thionyl chloride (0.27 mL) was heated with stirring to 40° C. for 0.5 h and subsequently cooled in the ice bath. The solid was isolated by filtration and washed with CH2Cl2 to give 4-[3-(4-chloromethyl-oxazol-2-yl)-phenyl]-8-pyrrol-1-yl-1,3-dihydro-benzo[b][1,4]diazepin-2-one (1.0 g) as yellow crystals.

Workup

  1. temperaturewas heated
  2. customThe solid was isolated by filtration
  3. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-659a1d44b89d448c8085c3c24cd9d241
Source dataset
uspto-grants-2003_04
Patent number
US06548495B2

Reaction notes

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