Sodium Hydroxide → 2-[Bis-(2-chloroethyl)amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid

HRID 1172503Notes

Reaction equation

HRID 1172503 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:8]=[C:9]([CH3:32])[C:10]2[O:16][C:15]3[C:17]([Cl:28])=[CH:18][C:19]([N:21]([CH2:25][CH2:26][Cl:27])[CH2:22][CH2:23][Cl:24])=[CH:20][C:14]=3[CH2:13][S:12](=[O:30])(=[O:29])[C:11]=2[CH:31]=1)=[O:6]>O1CCCC1>[Cl:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][Cl:27])[C:19]1[CH:18]=[C:17]([Cl:28])[C:15]2[O:16][C:10]3[C:9]([CH3:32])=[CH:8][C:7]([C:5]([OH:6])=[O:4])=[CH:31][C:11]=3[S:12](=[O:29])(=[O:30])[CH2:13][C:14]=2[CH:20]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 115260722-[Bis-(2-chloro-ethyl)-amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 1317284742-[Bis-(2-chloroethyl)amino]-4-chloro-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]-cycloheptene-8-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide (0.78 g, 19.6 mmol in 45 mL water) was added to a solution of Example 102 (3.21 g, 6.53 mmol) in tetrahydrofuran (45 mL). It was stirred for 3 h, partially concentrated, treated with dil. HCl to pH 7, filtered, washed with water and dried to obtain the title compound as a white solid. Yield: 3.01 g (97%). 1H NMR (CDCl3+DMSO-d6): δ 2.40 (s, 3H, CH3), 3.4 (t, 4H, 2CH2), 3.5 (t, 4H, 2CH2), 4.5 (s, 2H, CH2), 6.4 (d, 1H, Ar), 6.5 (d, 1H, Ar), 7.7 (d, 1H, Ar), 8.1 (d, 1H, Ar); MS: m/e (CI+) 478 (M+).

Workup

  1. concentrationpartially concentrated
  2. additiontreated with dil. HCl to pH 7
  3. filtrationfiltered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d8424e17c0ae4b2fa697ca1e23e8854b
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

Loading…