Methanol → HCID 54684946, compound

HRID 2164098Notes

Reaction equation

HRID 2164098 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12]([OH:23])=[C:13]([C:19]([O:21]C)=O)[N:14]([CH3:18])[S:15](=[O:17])(=[O:16])[C:5]=3[C:4]=2[CH:3]=1.[NH2:24][C:25]1[S:26][CH:27]=[CH:28][N:29]=1.B(OCCCC)(OCCCC)OCCCC.CO>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH3:11])[C:6]3[C:12]([OH:23])=[C:13]([C:19]([NH:24][C:25]4[S:26][CH:27]=[CH:28][N:29]=4)=[O:21])[N:14]([CH3:18])[S:15](=[O:17])(=[O:16])[C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 21552-AminothiazoleHCID 12712Tributyl borateHCID 54684967HCID 54684967, compound

Product 1

HCID 54684946HCID 54684946, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3.0 gm (8.4 millimols) of methyl 8-chloro-2,5-dihydro-2,5-dimethyl-4-hydroxy-1,2-thiazino[5,6-b]indole-3-carboxylate 1,1-dioxide, 0.9 gm (9 millimols) of 2-amino-thiazole and 50 mgm of tri-n-butyl borate were refluxed in 300 ml of dry xylene for 6 hours. The methanol released by the reaction was separated by means of a 4-A-molecular sieve in a Soxhlet-attachment. 3.1 gm of crystals were separated from the cooled reaction mixture by filtration and subsequently boiled in a mixture of 100 ml of acetonitrile and 1 ml of glacial acetic acid. After filtration and drying, 2.5 gm (68% of theory) of 8-chloro-2,5-dihydro-2,5-dimethyl-4-hydroxy-N-(2-thiazolyl)-1,2-thiazino[5,6-b]indole-3-carboxamide-1,1-dioxide were obtained; M.p.: 282° C. (decomposition).

Workup

  1. customwas separated by means of a 4-A-molecular sieve in a Soxhlet-attachment
  2. custom3.1 gm of crystals were separated from the cooled reaction mixture by filtration
  3. additionsubsequently boiled in a mixture of 100 ml of acetonitrile and 1 ml of glacial acetic acid
  4. filtrationAfter filtration
  5. customdrying

Sources & evidence

ORD record
ord-5c97779e1e604232b43b752633d85b4a
Source dataset
uspto-grants-1979_01
Patent number
US04137313

Reaction notes

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