1-Chloroethyl chloroformate → 5-hydroxy-12-(alpha-chloroethoxycarbonyl)-12H-benzo[a]phenothiazine

HRID 64971Notes

Reaction equation

HRID 64971 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=12.Cl[C:21]([O:23][CH:24]([Cl:26])[CH3:25])=[O:22]>O1CCCC1>[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([N:6]([C:21]([O:23][CH:24]([Cl:26])[CH3:25])=[O:22])[C:7]3[C:12]([S:13]2)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:16]=[CH:17][CH:18]=[CH:19][C:3]=12

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 137124785-hydroxy-12H-benzo[a]phenothiazine

Product 1

HCID 146014145-hydroxy-12-(alpha-chloroethoxycarbonyl)-12H-benzo[a]phenothiazineYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-hydroxy-12H-benzo[a]phenothiazine (5 g) and α-chloroethyl chloroformate (10 g) in tetrahydrofuran (20 ml) was refluxed for 9 hours, then the volatile components were evaporated away and the residue chromatographed on a column of silica gel, eluting with a 1:9 ethyl acetate-hexane mixture to afford the title compound (4 g) as an oil.

Workup

  1. temperaturewas refluxed for 9 hours
  2. customthe volatile components were evaporated away
  3. customthe residue chromatographed on a column of silica gel
  4. washeluting with a 1:9 ethyl acetate-hexane mixture

Sources & evidence

ORD record
ord-cab51a59a48040a185db02e56db36842
Source dataset
uspto-grants-1986_09
Patent number
US04611056

Reaction notes

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